Inter- vs. Intra-Molecular Hydrogen Bond in Complexes of Nitrophthalic Acids with Pyridine
This study covers the analysis of isomeric forms of nitrophthalic acids with pyridine. This work dwells on the complementary experimental (X-ray, IR and Raman) and theoretical (Car-Parrinello Molecular Dynamics (CPMD) and Density Functional Theory (DFT)) studies of the obtained complexes. The conduc...
Saved in:
| Published in | International journal of molecular sciences Vol. 24; no. 6; p. 5248 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Switzerland
MDPI AG
09.03.2023
MDPI |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | This study covers the analysis of isomeric forms of nitrophthalic acids with pyridine. This work dwells on the complementary experimental (X-ray, IR and Raman) and theoretical (Car-Parrinello Molecular Dynamics (CPMD) and Density Functional Theory (DFT)) studies of the obtained complexes. The conducted studies showed that steric repulsion between the nitro group in ortho-position and the carboxyl group causes significant isomeric changes. Modeling of the nitrophthalic acid-pyridine complex yielded a short strong intramolecular hydrogen bond (SSHB). The transition energy from the isomeric form with an intermolecular hydrogen bond to the isomeric form with an intramolecular hydrogen bond was estimated. |
|---|---|
| AbstractList | This study covers the analysis of isomeric forms of nitrophthalic acids with pyridine. This work dwells on the complementary experimental (X-ray, IR and Raman) and theoretical (Car-Parrinello Molecular Dynamics (CPMD) and Density Functional Theory (DFT)) studies of the obtained complexes. The conducted studies showed that steric repulsion between the nitro group in ortho-position and the carboxyl group causes significant isomeric changes. Modeling of the nitrophthalic acid—pyridine complex yielded a short strong intramolecular hydrogen bond (SSHB). The transition energy from the isomeric form with an intermolecular hydrogen bond to the isomeric form with an intramolecular hydrogen bond was estimated. |
| Audience | Academic |
| Author | Jezierska, Aneta Filarowski, Aleksander Kochel, Andrzej Jóźwiak, Kinga Panek, Jarosław J |
| AuthorAffiliation | Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland |
| AuthorAffiliation_xml | – name: Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland |
| Author_xml | – sequence: 1 givenname: Kinga orcidid: 0000-0002-8010-6942 surname: Jóźwiak fullname: Jóźwiak, Kinga organization: Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland – sequence: 2 givenname: Aneta orcidid: 0000-0001-6601-9124 surname: Jezierska fullname: Jezierska, Aneta organization: Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland – sequence: 3 givenname: Jarosław J orcidid: 0000-0002-2952-9739 surname: Panek fullname: Panek, Jarosław J organization: Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland – sequence: 4 givenname: Andrzej orcidid: 0000-0001-7433-9996 surname: Kochel fullname: Kochel, Andrzej organization: Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland – sequence: 5 givenname: Aleksander orcidid: 0000-0003-1013-4945 surname: Filarowski fullname: Filarowski, Aleksander organization: Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36982321$$D View this record in MEDLINE/PubMed |
| BookMark | eNpdkruPEzEQxlfoEPeAjhpZoqFgg99rVyhEwEU6HgU0NJbXnk0c7a6DvTnIf49DjlMOufBo_JvPnvF3WZ2NcYSqek7wjDGN34TNkCnHUlCuHlUXhFNaYyybs5P4vLrMeYMxZVToJ9U5k1qVmFxUP5bjBKlGt3mGSphs_Sn24Ha9Teh671NcwYjexdGjMKJFHLY9_IaMYoc-hynF7Xpa2z44NHfBZ_QrTGv0dZ-CDyM8rR53ts_w7G6_qr5_eP9tcV3ffPm4XMxvaieImupWN1ozDqzF3DICIEBLjilnoLVWHWsYkFZz6rnQlAvcESZ9YzuqGtkyxa6q5VHXR7sx2xQGm_Ym2mD-JmJaGZum4HowrVIghJAEGs45bm3LvfNKaCmxbeRB6-1Ra7trB_AODiPpH4g-PBnD2qzirSEYc6UkKwqv7hRS_LmDPJkhZAd9b0eIu2xoo6nAXEpS0Jf_oZu4S2OZ1YEiUnAlm0LNjtTKlg7C2MVysSvLwxBc8UIXSn7eCKKpLP9bCl4fC1yKOSfo7p9PsDlYxpxapuAvTlu-h_95hP0B6dG7-A |
| CitedBy_id | crossref_primary_10_1016_j_saa_2024_124585 |
| Cites_doi | 10.1016/j.saa.2015.04.052 10.3390/molecules22040552 10.1007/978-981-10-1139-9 10.1039/c0cc04707d 10.1103/PhysRevB.37.785 10.1021/jo035350t 10.1023/A:1008193805436 10.1016/j.molliq.2020.113910 10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U 10.1039/C9CE00925F 10.1063/1.464913 10.1016/j.molstruc.2005.03.034 10.1016/j.molstruc.2004.01.033 10.1103/PhysRev.140.A1133 10.1126/science.8009219 10.1002/poc.1437 10.2174/1385272822666181015143916 10.1002/jcc.20495 10.1021/acs.cgd.0c00023 10.1021/jo201639k 10.1103/PhysRevA.31.1695 10.1080/10610278.2011.575470 10.1007/s10822-012-9597-3 10.1021/jp1063116 10.3390/molecules25204720 10.1107/S0108767307043930 10.1063/1.472933 10.1039/c2ce25128k 10.1039/C8NJ04339F 10.1002/chem.202201093 10.1063/1.447079 10.1016/j.molstruc.2005.10.046 10.1016/0263-7855(96)00018-5 10.1039/b006879i 10.3390/molecules21121657 10.1016/j.molliq.2021.118052 10.1146/annurev.biophys.30.1.1 10.1039/C8RA03042A 10.1007/s10870-014-0534-2 10.1063/1.447334 10.1103/PhysRev.136.B864 10.1002/mrc.1260320705 10.1002/slct.202002745 10.3390/sym13030425 10.1039/ft9969205051 10.1021/jp1084857 10.1016/S0022-2860(00)00487-7 10.3390/catal9110909 10.1103/PhysRevB.43.1993 10.1021/acs.cgd.1c00619 10.1016/S1386-1425(98)00348-5 10.1021/acs.joc.0c03008 10.1016/S0167-7322(01)00305-1 |
| ContentType | Journal Article |
| Copyright | COPYRIGHT 2023 MDPI AG 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2023 by the authors. 2023 |
| Copyright_xml | – notice: COPYRIGHT 2023 MDPI AG – notice: 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. – notice: 2023 by the authors. 2023 |
| DBID | CGR CUY CVF ECM EIF NPM AAYXX CITATION 3V. 7X7 7XB 88E 8FI 8FJ 8FK 8G5 ABUWG AFKRA AZQEC BENPR CCPQU DWQXO FYUFA GHDGH GNUQQ GUQSH K9. M0S M1P M2O MBDVC PIMPY PQEST PQQKQ PQUKI PRINS Q9U 7X8 5PM DOA |
| DOI | 10.3390/ijms24065248 |
| DatabaseName | Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef ProQuest Central (Corporate) ProQuest Health & Medical Collection ProQuest Central (purchase pre-March 2016) Medical Database (Alumni Edition) Hospital Premium Collection Hospital Premium Collection (Alumni Edition) ProQuest Central (Alumni) (purchase pre-March 2016) Research Library (Alumni Edition) ProQuest Central (Alumni) ProQuest Central ProQuest Central Essentials ProQuest Central ProQuest One Community College ProQuest Central Korea Health Research Premium Collection Health Research Premium Collection (Alumni) ProQuest Central Student Research Library Prep ProQuest Health & Medical Complete (Alumni) Health & Medical Collection (Alumni Edition) Medical Database ProQuest Research Library Research Library (Corporate) Publicly Available Content Database ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central China ProQuest Central Basic MEDLINE - Academic PubMed Central (Full Participant titles) DOAJ Directory of Open Access Journals |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef Publicly Available Content Database Research Library Prep ProQuest Central Student ProQuest Central Essentials ProQuest Health & Medical Complete (Alumni) ProQuest Central (Alumni Edition) ProQuest One Community College Research Library (Alumni Edition) ProQuest Central China ProQuest Central Health Research Premium Collection Health and Medicine Complete (Alumni Edition) ProQuest Central Korea ProQuest Research Library ProQuest Medical Library (Alumni) ProQuest Central Basic ProQuest One Academic Eastern Edition ProQuest Hospital Collection Health Research Premium Collection (Alumni) ProQuest Hospital Collection (Alumni) ProQuest Health & Medical Complete ProQuest Medical Library ProQuest One Academic UKI Edition ProQuest One Academic ProQuest Central (Alumni) MEDLINE - Academic |
| DatabaseTitleList | Publicly Available Content Database MEDLINE CrossRef |
| Database_xml | – sequence: 1 dbid: DOA name: DOAJ, Directory of Open Access Journals url: https://www.doaj.org/ sourceTypes: Open Website – sequence: 2 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 3 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database – sequence: 4 dbid: BENPR name: ProQuest Central url: https://www.proquest.com/central sourceTypes: Aggregation Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Biology |
| EISSN | 1422-0067 |
| ExternalDocumentID | oai_doaj_org_article_b88e55561e74440bab4dcd859660a768 A751926325 10_3390_ijms24065248 36982321 |
| Genre | Journal Article |
| GeographicLocations | United Kingdom Germany |
| GeographicLocations_xml | – name: United Kingdom – name: Germany |
| GroupedDBID | --- 29J 2WC 3V. 53G 5GY 5VS 7X7 88E 8FE 8FG 8FH 8FI 8FJ 8G5 A8Z AADQD AAFWJ AAHBH ABDBF ABJCF ABUWG ACGFO ACIHN ACIWK ACPRK ADBBV AEAQA AENEX AFKRA AFPKN AFZYC ALIPV ALMA_UNASSIGNED_HOLDINGS AOIJS AZQEC BAWUL BBNVY BCNDV BENPR BHPHI BPHCQ BVXVI CCPQU CGR CS3 CUY CVF D1I DIK DU5 DWQXO E3Z EBD EBS ECM EIF EJD ESTFP ESX F5P FRP FYUFA GNUQQ GROUPED_DOAJ GUQSH GX1 HCIFZ HH5 HMCUK HYE IAO ITC KB. KQ8 LK8 M1P M2O M48 M7P MODMG M~E NPM O5R O5S OK1 P2P PDBOC PIMPY PQQKQ PROAC PSQYO RIG RNS RPM TR2 TUS UKHRP ~8M AAYXX CITATION BGLVJ 7XB 8FK K9. MBDVC PQEST PQUKI PRINS Q9U 7X8 5PM |
| ID | FETCH-LOGICAL-c518t-b979934e3b04a31ee5e9640243e9998f373e1b942d4592450f136d7af2876b383 |
| IEDL.DBID | RPM |
| ISSN | 1422-0067 1661-6596 |
| IngestDate | Fri Jul 05 11:56:20 EDT 2024 Tue Sep 17 21:35:24 EDT 2024 Fri Aug 16 07:52:47 EDT 2024 Fri Sep 13 02:13:07 EDT 2024 Fri Feb 02 04:17:27 EST 2024 Fri Aug 23 01:58:57 EDT 2024 Sat Sep 28 08:18:42 EDT 2024 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 6 |
| Keywords | steric repulsion DFT proton dynamics IR Raman CPMD X-ray phthalic acid hydrogen bond |
| Language | English |
| License | Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c518t-b979934e3b04a31ee5e9640243e9998f373e1b942d4592450f136d7af2876b383 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-2952-9739 0000-0003-1013-4945 0000-0002-8010-6942 0000-0001-6601-9124 0000-0001-7433-9996 |
| OpenAccessLink | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10048863/ |
| PMID | 36982321 |
| PQID | 2791654867 |
| PQPubID | 2032341 |
| ParticipantIDs | doaj_primary_oai_doaj_org_article_b88e55561e74440bab4dcd859660a768 pubmedcentral_primary_oai_pubmedcentral_nih_gov_10048863 proquest_miscellaneous_2792504661 proquest_journals_2791654867 gale_infotracacademiconefile_A751926325 crossref_primary_10_3390_ijms24065248 pubmed_primary_36982321 |
| PublicationCentury | 2000 |
| PublicationDate | 20230309 |
| PublicationDateYYYYMMDD | 2023-03-09 |
| PublicationDate_xml | – month: 3 year: 2023 text: 20230309 day: 9 |
| PublicationDecade | 2020 |
| PublicationPlace | Switzerland |
| PublicationPlace_xml | – name: Switzerland – name: Basel |
| PublicationTitle | International journal of molecular sciences |
| PublicationTitleAlternate | Int J Mol Sci |
| PublicationYear | 2023 |
| Publisher | MDPI AG MDPI |
| Publisher_xml | – name: MDPI AG – name: MDPI |
| References | Nowok (ref_15) 2022; 348 Wilson (ref_48) 1996; 92 Lee (ref_68) 1993; 37 Glidewell (ref_27) 2003; C59 Hansen (ref_5) 1994; 32 ref_11 Sheldrick (ref_51) 2015; C71 ref_53 ref_52 Hohenberg (ref_54) 1964; 136 Hansen (ref_38) 2022; 28 Pozharskii (ref_2) 2003; 68 Humphrey (ref_62) 1996; 14 ref_16 Kool (ref_36) 2001; 30 Jin (ref_30) 2014; 44 Hockney (ref_56) 1970; 9 Liu (ref_13) 2020; 20 Tiznado (ref_39) 2011; 76 Perdew (ref_57) 1996; 105 Zhoujin (ref_34) 2021; 21 ref_65 Ozeryanskii (ref_4) 2021; 86 ref_20 Sheldrick (ref_50) 2008; A64 ref_64 ref_63 Kwocz (ref_8) 2018; 42 Cai (ref_47) 2012; 14 Cleland (ref_41) 1994; 264 Becke (ref_67) 1993; 98 Kolehmainen (ref_25) 2010; 114 Bolvig (ref_6) 2005; 749 Grimme (ref_61) 2006; 27 (ref_59) 1984; 81 Hoover (ref_60) 1985; 31 ref_35 Iogansen (ref_42) 1999; 55 ref_33 ref_32 Kolehmainen (ref_21) 2011; 23 Smith (ref_28) 2008; C64 Kwiatkowski (ref_23) 2018; 42 Schaftenaar (ref_69) 2000; 14 Kohn (ref_55) 1965; 140 Saunders (ref_31) 2019; 21 Majewska (ref_17) 2009; 22 Kolehmainen (ref_24) 2000; 11 Kozlecki (ref_18) 2015; 149 Buemi (ref_1) 1997; 2 (ref_22) 2018; 22 Steiner (ref_44) 2002; 41 ref_46 Troullier (ref_58) 1991; 43 Martyniak (ref_9) 2012; 9 ref_45 Hussain (ref_12) 2020; 317 ref_40 Frisch (ref_66) 1984; 80 Poater (ref_37) 2011; 47 Sobczyk (ref_43) 2000; 552 Filatova (ref_3) 2020; 5 Kawski (ref_19) 2006; 790 Filarowski (ref_10) 2004; 700 ref_49 Huelsekopf (ref_14) 2002; 98–99 ref_7 Kolehmainen (ref_26) 2010; 114 Smith (ref_29) 2011; C67 |
| References_xml | – ident: ref_49 – volume: 149 start-page: 254 year: 2015 ident: ref_18 article-title: Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring publication-title: Spectrochim. Acta A doi: 10.1016/j.saa.2015.04.052 contributor: fullname: Kozlecki – ident: ref_7 doi: 10.3390/molecules22040552 – ident: ref_35 doi: 10.1007/978-981-10-1139-9 – volume: 47 start-page: 7326 year: 2011 ident: ref_37 article-title: Selectivity in DNA replication. Interplay of steric shape, hydrogen bonds, p-stacking and solvent effects publication-title: Chem. Commun. doi: 10.1039/c0cc04707d contributor: fullname: Poater – ident: ref_65 – volume: 37 start-page: B785 year: 1993 ident: ref_68 article-title: Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density publication-title: Phys. Rev. doi: 10.1103/PhysRevB.37.785 contributor: fullname: Lee – volume: 68 start-page: 10109 year: 2003 ident: ref_2 article-title: Organometallic Synthesis, Molecular Structure, and Coloration of 2,7-Disubstituted 1,8-Bis(dimethylamino)naphthalenes. How Significant Is the Influence of “Buttressing Effect” on Their Basicity? publication-title: J. Org. Chem. doi: 10.1021/jo035350t contributor: fullname: Pozharskii – volume: 14 start-page: 123 year: 2000 ident: ref_69 article-title: Molden: A pre- and post-processing program for molecular and electronic structures publication-title: J. Comput.-Aided Mol. Des. doi: 10.1023/A:1008193805436 contributor: fullname: Schaftenaar – volume: 317 start-page: 2 year: 2020 ident: ref_12 article-title: Steric effect in the formation of hydrogen bonded complexes of isopropylamine with alicyclic ethers by ultrasonic and DFT approach publication-title: J. Mol. Liq. doi: 10.1016/j.molliq.2020.113910 contributor: fullname: Hussain – volume: 41 start-page: 48 year: 2002 ident: ref_44 article-title: The Hydrogen Bond in the Solid State publication-title: Angew. Chem. Int. Ed. doi: 10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U contributor: fullname: Steiner – volume: C71 start-page: 3 year: 2015 ident: ref_51 article-title: Crystal Structure Refinement with SHELXL publication-title: Acta Cryst. contributor: fullname: Sheldrick – volume: 21 start-page: 5249 year: 2019 ident: ref_31 article-title: Exploring short strong hydrogen bonds engineered in organic acid molecular crystals for temperature dependent proton migration behaviour using single crystal synchrotron X-ray diffraction (SCSXRD) publication-title: CrystEngComm doi: 10.1039/C9CE00925F contributor: fullname: Saunders – volume: 98 start-page: 5648 year: 1993 ident: ref_67 article-title: Density-functional thermochemistry. III. The role of exact exchange publication-title: J. Chem. Phys. doi: 10.1063/1.464913 contributor: fullname: Becke – volume: 749 start-page: 155 year: 2005 ident: ref_6 article-title: Steric compression effects of intramolecularly hydrogen bonded o-hydroxy acyl aromatics. An X-ray and 13C-NMR study publication-title: J. Mol. Struct. doi: 10.1016/j.molstruc.2005.03.034 contributor: fullname: Bolvig – ident: ref_52 – volume: 700 start-page: 67 year: 2004 ident: ref_10 article-title: The intramolecular hydrogen bond in ortho-hydroxy acetophenones publication-title: J. Mol. Struct. doi: 10.1016/j.molstruc.2004.01.033 contributor: fullname: Filarowski – volume: 140 start-page: A1133 year: 1965 ident: ref_55 article-title: Self-Consistent Equations Including Exchange and Correlation Effects publication-title: Phys. Rev. doi: 10.1103/PhysRev.140.A1133 contributor: fullname: Kohn – volume: 264 start-page: 1887 year: 1994 ident: ref_41 article-title: Low-barrier hydrogen-bonds and enzymatic catalysis publication-title: Science doi: 10.1126/science.8009219 contributor: fullname: Cleland – volume: 2 start-page: 302 year: 1997 ident: ref_1 article-title: Importance of steric effect on the hydrogen bond strength of malondialdehyde and acetylacetone 3-substituted derivatives. An ab initio study publication-title: J. Theor. Chem. contributor: fullname: Buemi – volume: 22 start-page: 130 year: 2009 ident: ref_17 article-title: Intra- versus intermolecular hydrogen bonding equilibrium in 2-hydroxy-N,N-diethylbenzamide publication-title: J. Phys. Org. Chem. doi: 10.1002/poc.1437 contributor: fullname: Majewska – ident: ref_45 – volume: 22 start-page: 2182 year: 2018 ident: ref_22 article-title: Conformational equilibrium and substituent effects in hydrogen-bonded complexes publication-title: Curr. Org. Chem. doi: 10.2174/1385272822666181015143916 – volume: 27 start-page: 1787 year: 2006 ident: ref_61 article-title: Semiempirical {GGA}-type density functional constructed with a long-range dispersion correction publication-title: J. Comput. Chem. doi: 10.1002/jcc.20495 contributor: fullname: Grimme – volume: 20 start-page: 4346 year: 2020 ident: ref_13 article-title: Steric Effect Determines the Formation of Lactam−Lactam Dimers or Amide C=O···NH (Lactam) Chain Motifs in N-Phenyl-2-Hydroxynicotinanilides publication-title: Cryst. Growth Des. doi: 10.1021/acs.cgd.0c00023 contributor: fullname: Liu – ident: ref_20 – ident: ref_53 – volume: 76 start-page: 8913 year: 2011 ident: ref_39 article-title: An Analysis of the Isomerization Energies of 1,2-/1,3-Diazacyclobutadiene, Pyrazole/Imidazole, and Pyridazine/Pyrimidine with the Turn-Upside-Down Approach publication-title: J. Org. Chem. doi: 10.1021/jo201639k contributor: fullname: Tiznado – volume: C64 start-page: o123 year: 2008 ident: ref_28 article-title: The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids publication-title: Acta Cryst. contributor: fullname: Smith – volume: 31 start-page: 1695 year: 1985 ident: ref_60 article-title: Canonical dynamics: Equilibrium phase-space distributions publication-title: Phys. Rev. A doi: 10.1103/PhysRevA.31.1695 contributor: fullname: Hoover – volume: 23 start-page: 579 year: 2011 ident: ref_21 article-title: Tuning the hydrogen-bonding strength in 2,6-bis(cycloalkylcarbonylamino)pyridine assemblies by variable flexibility. Association constants measured by hydrogen-bonded vs. non-hydrogen-bonded protons publication-title: Supramol. Chem. doi: 10.1080/10610278.2011.575470 contributor: fullname: Kolehmainen – volume: 9 start-page: 1045 year: 2012 ident: ref_9 article-title: Triple hydrogen bonding in a circular arrangement: Ab initio, DFT and first-principles MD studies of tris-hydroxyaryl enamines publication-title: J. Comp.-Aided Mol. Des. doi: 10.1007/s10822-012-9597-3 contributor: fullname: Martyniak – volume: 114 start-page: 10421 year: 2010 ident: ref_25 article-title: Self-Organization of 2-Acylaminopyridines in the Solid State and in Solution publication-title: J. Phys. Chem. A doi: 10.1021/jp1063116 contributor: fullname: Kolehmainen – ident: ref_33 doi: 10.3390/molecules25204720 – volume: A64 start-page: 112 year: 2008 ident: ref_50 article-title: Short History of SHELX publication-title: Acta Cryst. doi: 10.1107/S0108767307043930 contributor: fullname: Sheldrick – volume: C67 start-page: o259 year: 2011 ident: ref_29 article-title: Proton-transfer compounds of isonipecotamide with the aromatic dicarboxylic acids 4-nitrophthalic, 4,5-dichlorophthalic, 5-nitroisophthalic and terephthalic acid publication-title: Acta Cryst. contributor: fullname: Smith – ident: ref_40 – volume: 105 start-page: 9982 year: 1996 ident: ref_57 article-title: Rationale for mixing exact exchange with density functional approximations publication-title: J. Chem. Phys. doi: 10.1063/1.472933 contributor: fullname: Perdew – volume: 14 start-page: 4420 year: 2012 ident: ref_47 article-title: Pressure effects on H-ordering in hydrogen bonds and interactions in benzoic acid publication-title: CrystEngComm doi: 10.1039/c2ce25128k contributor: fullname: Cai – ident: ref_63 – volume: 42 start-page: 19467 year: 2018 ident: ref_8 article-title: A molecular roundabout: Triple cycle-arranged hydrogen bonds in light of experiment and theory publication-title: New J. Chem. doi: 10.1039/C8NJ04339F contributor: fullname: Kwocz – volume: 28 start-page: e202201093 year: 2022 ident: ref_38 article-title: C-X Bond Activation by Palladium: Steric Shielding versus Steric Attraction publication-title: Chem. Eur. J. doi: 10.1002/chem.202201093 contributor: fullname: Hansen – volume: 80 start-page: 3265 year: 1984 ident: ref_66 article-title: Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets publication-title: J. Chem. Phys. doi: 10.1063/1.447079 contributor: fullname: Frisch – volume: 790 start-page: 65 year: 2006 ident: ref_19 article-title: The intramolecular hydrogen bond in 2-hydroxy-benzamides publication-title: J. Mol. Struct. doi: 10.1016/j.molstruc.2005.10.046 contributor: fullname: Kawski – volume: 9 start-page: 135 year: 1970 ident: ref_56 article-title: The potential calculation and some applications publication-title: Meth. Comput. Phys. contributor: fullname: Hockney – volume: 14 start-page: 33 year: 1996 ident: ref_62 article-title: Visual Molecular Dynamics publication-title: J. Mol. Graph. doi: 10.1016/0263-7855(96)00018-5 contributor: fullname: Humphrey – volume: 11 start-page: 2185 year: 2000 ident: ref_24 article-title: Substituent and temperature controlled tautomerism of 2-phenacylpyridine: The hydrogen bond as a configurational lock of (Z)-2-(2-hydroxy-2-phenylvinyl)pyridine publication-title: J. Chem. Soc. Perkin Trans. 2 doi: 10.1039/b006879i contributor: fullname: Kolehmainen – ident: ref_11 doi: 10.3390/molecules21121657 – volume: 348 start-page: 118052 year: 2022 ident: ref_15 article-title: Glass-forming Schiff bases: Peculiar self-organizing systems with bifurcated hydrogen bonds publication-title: J. Mol. Liq. doi: 10.1016/j.molliq.2021.118052 contributor: fullname: Nowok – volume: 30 start-page: 1 year: 2001 ident: ref_36 article-title: Hydrogen Bonding, Base Stacking, and Steric Effects in DNA Replication publication-title: Ann. Rev. Biophys. Biomol. Struct. doi: 10.1146/annurev.biophys.30.1.1 contributor: fullname: Kool – volume: 42 start-page: 23698 year: 2018 ident: ref_23 article-title: The trans/cis photoisomerization in hydrogen bonded complexes with stability controlled by substituent effects: 3-(6-aminopyridin-3-yl) acrylate case study publication-title: RSC Adv. doi: 10.1039/C8RA03042A contributor: fullname: Kwiatkowski – ident: ref_46 – volume: 44 start-page: 435 year: 2014 ident: ref_30 article-title: Crystal and Molecular Structure of Two Proton Transfer Compounds from Quinolin-8-ol, 4-nitro-phthalic Acid, and 1,5-Naphthalenedisulfonic Acid publication-title: J. Chem. Crystallogr. doi: 10.1007/s10870-014-0534-2 contributor: fullname: Jin – volume: 81 start-page: 511 year: 1984 ident: ref_59 article-title: A unified formulation of the constant temperature molecular dynamics methods publication-title: J. Chem. Phys. doi: 10.1063/1.447334 – volume: 136 start-page: B864 year: 1964 ident: ref_54 article-title: Inhomogeneous Electron Gas publication-title: Phys. Rev. doi: 10.1103/PhysRev.136.B864 contributor: fullname: Hohenberg – volume: 32 start-page: 399 year: 1994 ident: ref_5 article-title: Deuterium and 18O isotope effects on 13C chemical shifts of sterically hindered and/or intra-molecularly hydrogen-bonded o-hydroxy acyl aromatics publication-title: Magn. Res. Chem. doi: 10.1002/mrc.1260320705 contributor: fullname: Hansen – ident: ref_64 – volume: 5 start-page: 9932 year: 2020 ident: ref_3 article-title: Synthesis of 2-Aryl- and 2,7-Diaryl-1,8-bis(dimethylamino)naphthalenes. Overview of the “Buttressing effect” in 2,7-Disubstituted Proton Sponges publication-title: ChemistrySelect doi: 10.1002/slct.202002745 contributor: fullname: Filatova – ident: ref_32 doi: 10.3390/sym13030425 – volume: 92 start-page: 5051 year: 1996 ident: ref_48 article-title: A single-crystal neutron diffraction study of the temperature dependence of hydrogen-atom disorder in benzoic acid dimers publication-title: J. Chem. Soc. Faraday Trans. doi: 10.1039/ft9969205051 contributor: fullname: Wilson – volume: 114 start-page: 12881 year: 2010 ident: ref_26 article-title: Complexation of 2,6-Bis(acylamino)pyridines with Dipyridin-2-Ylamine and 4,4-Dimethylpiperidine-2,6-Dione publication-title: J. Phys. Chem. A doi: 10.1021/jp1084857 contributor: fullname: Kolehmainen – volume: C59 start-page: o144 year: 2003 ident: ref_27 article-title: 3-Nitrophthalic acid: C(4) and R22(8) motifs of O-H…O hydrogen bonds generate sheets which are linked by C-H…O hydrogen bonds publication-title: Acta Cryst. contributor: fullname: Glidewell – volume: 552 start-page: 233 year: 2000 ident: ref_43 article-title: The OHN hydrogen bonding in the adduct of 2,4-dinitrobenzoic acid with pyridine. Low temperature X-ray diffraction and IR spectroscopic studies publication-title: J. Mol. Struct. doi: 10.1016/S0022-2860(00)00487-7 contributor: fullname: Sobczyk – ident: ref_16 doi: 10.3390/catal9110909 – volume: 43 start-page: 1993 year: 1991 ident: ref_58 article-title: Efficient pseudopotentials for plane-wave calculations publication-title: Phys. Rev. B doi: 10.1103/PhysRevB.43.1993 contributor: fullname: Troullier – volume: 21 start-page: 6155 year: 2021 ident: ref_34 article-title: Synthon Polymorphism and π–π Stacking in N-Phenyl-2-hydroxynicotinanilides publication-title: Cryst. Growth Des. doi: 10.1021/acs.cgd.1c00619 contributor: fullname: Zhoujin – volume: 55 start-page: 1585 year: 1999 ident: ref_42 article-title: Direct proportionality of the hydrogen bonding energy and the intensification of the stretching v(XH) vibration in infrared spectra publication-title: Spectr. Acta A doi: 10.1016/S1386-1425(98)00348-5 contributor: fullname: Iogansen – volume: 86 start-page: 3637 year: 2021 ident: ref_4 article-title: Combination of “buttressing” and “clothespin” effects for reaching the shortest NHN hydrogen bond in proton sponge cations publication-title: J. Org. Chem. doi: 10.1021/acs.joc.0c03008 contributor: fullname: Ozeryanskii – volume: 98–99 start-page: 163 year: 2002 ident: ref_14 article-title: Hydrogen Bonding in a sterically hindered alcohol publication-title: J. Mol. Liq. doi: 10.1016/S0167-7322(01)00305-1 contributor: fullname: Huelsekopf |
| SSID | ssj0023259 |
| Score | 2.4292881 |
| Snippet | This study covers the analysis of isomeric forms of nitrophthalic acids with pyridine. This work dwells on the complementary experimental (X-ray, IR and Raman)... |
| SourceID | doaj pubmedcentral proquest gale crossref pubmed |
| SourceType | Open Website Open Access Repository Aggregation Database Index Database |
| StartPage | 5248 |
| SubjectTerms | Acids Alzheimer's disease Bonds Carboxyl group Chemical bonds Density functional theory Density functionals Hydrogen Hydrogen - chemistry hydrogen bond Hydrogen Bonding Hydrogen bonds Isomerism Molecular dynamics Molecular Dynamics Simulation phthalic acid Proteins proton dynamics Protons Pyridine Pyridines Pyridines - chemistry Simulation steric repulsion X-ray |
| SummonAdditionalLinks | – databaseName: DOAJ Directory of Open Access Journals dbid: DOA link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1Na9wwEBUhUMil9CNt3aZFhYSe1KytTx-3JWFbSMihgdCLsGSZdWntsHZK9t9nRvYuXnLopVdLGHlmpJlnSe8Rcuxz4Y30jkHqlkzwSqOQu2dBe8RAudAK7ztfXKrFtfh-I28mUl94JmygBx4Md-qMCRI1HIMWQsxc4UTpSyORVbKAWjmuvqncgKkRavEsyqSlkH2Ygr7DkXcOAP-0_vWnwzQmM9T8mSSjyNn_eGWepKbdY5OTPHT-jDwdC0g6Hwb-nOyF5gV5MkhKrl-Sn_EXH6N_u8_0G76AXWwEcOliXa5aCBiKWsK0biguBr_DfehoW9HLul-1t8t-CZW5p3Nflx3Fv7T0ar2qIcOFQ3J9fvbj64KN-gnMy9T0zOGWHReBu5koeBqCDLkSSEEYoCw0Fdc8pC4XWSkkwDA5q1KuSl1UgKKUA-j6iuw3bRPeEJqVGRRqeeZnWD8JFEqH1FapwnkEQC4hJxtD2tuBJsMCvECD26nBE_IFrbztg-TW8QG43I4ut_9yeUI-oY8sTkGwoy_GmwQwVCSzsnMNZSny0MuEHG3caMe52dlM53iFyyidkI_bZphVuFVSNKG9i32Q2w3CJyGvB69vx8xVbiDAoMXsxMPOR-22NPUyMnenccFU_O3_MMM7cpBBpMcDcfkR2e9Xd-E9VEi9-xAnwwNxZwmp priority: 102 providerName: Directory of Open Access Journals – databaseName: ProQuest Technology Collection dbid: 8FG link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3fi9QwEB7OE8EX8bfVUyIoPsXdNj_aPskqrqtwhw8eHL6UJk1vK9qubU_c_96ZtF13EXxtSkmTycx8Seb7AF7YVNpEWcMxdCsuRRmTkLvlLraEgVIZa6p3Pj3Tq3P56UJdHMFqqoWha5WTT_SOumgs7ZHPojilwptEx7Pc0C6A7WdvNj856UfROesopnENrofEiUc148sPO-glIi-bFmI04lqlergCLxDwz6pvPzoKayoiDaC94OQ5_P_11Huh6vAa5V5cWt6GW2NCyRaDBdyBI1ffhRuDxOT2Hnz1W36c_epes4_0AX46CeKy1bZoGzQgRtrCrKoZOYfv7rfrWFOys6pvm826X2OmbtnCVkXHaNeWfd62FUY8dx_Ol--_vFvxUU-BWxUmPTd0hCekE2YucxE6p1yqJVESOkwTk1LEwoUmlVEhFcIyNS9DoYs4LxFVaYNQ9gEc103tHgGLiggTtzSyc8qnJAmnY6grdW4sASITwMtpILPNQJuRIdygAc_2BzyAtzTKu3eI7No_aNrLbFw7mUkSp0jG08VSyrnJjSxskSgiFs0RLgXwiuYooyVJhpGPlQXYVSK3yhYxpqnES68COJmmMRvXapf9tawAnu-acZXR0Uleu-bKv0Ncb2g-ATwcZn3XZ6HTBA0MW5IDezj4qcOWulp7Ju_QO1AtHv-_X0_gJqnc-6tv6Qkc9-2Ve4q5UG-eeTP_A_DsBYo priority: 102 providerName: ProQuest – databaseName: Scholars Portal Journals: Open Access dbid: M48 link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwdV1Nb9QwEB2VIlAviO8GCjISiFPKJrYT54DQgqgWpK04sFLFxYodhw0qSZukqPvvmcnHaqPCdeNE2fHY815svwfw2ibCKmmNj6Vb-oLnMRm5W9_FljhQIuKIzjsvT6PFSnw9k2d7MLqNDgFs_kntyE9qVZ8fX19uPuCAf0-MEyn7u-LX74YKkwyFugW3Q8EF5fpSbNcTEDbIpN_2fuOOA7jLo0Rhk2BSmzoJ_5sT9U6lmu6i3ClLJ_fh3oAn2bxPgAew58qHcKd3mNw8gh_dFz-f_WmO2Rd6gL8c_XDZYpPVFeYPI2thVpSM5oZzd-0aVuXstGjr6mLdrhGoWza3RdYw-mjLvm3qAgueewyrk8_fPy38wU7BtzJQrW9oBY8Lx81MpDxwTrokEqRI6BAlqpzH3AUmEWEmJLIyOcsDHmVxmiOpigwy2SewX1alOwQWZiHitiS0M4JTgnzTsdLlUWos8SHjwZsxkPqiV83QyDYo9no39h58pChv25DWdfdDVf_Uw9DRRiknycXTxUKImUmNyGymJOmKpsiWPHhLfaQpRzCONh0OFuCrkraVnseIUkmWXnpwNHajHjNNh3FCJ7pUFHvwansZBxmtnKSlq666NiT1hljGg6d9r2_feUweD9QkHyZ_anqlLNadkHfQzZ8Rf_bfhz6HA_K37za9JUew39ZX7gWioNa87BL8LzHnAls priority: 102 providerName: Scholars Portal |
| Title | Inter- vs. Intra-Molecular Hydrogen Bond in Complexes of Nitrophthalic Acids with Pyridine |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/36982321 https://www.proquest.com/docview/2791654867/abstract/ https://search.proquest.com/docview/2792504661 https://pubmed.ncbi.nlm.nih.gov/PMC10048863 https://doaj.org/article/b88e55561e74440bab4dcd859660a768 |
| Volume | 24 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Ni9swEBW7Wwq9lH7X7dao0NKTk9iSLPmYXTZNCwmhdCH0YixZblw2drC9pfn3nfFHSOitEHyInKCMZjLvyaM3hHwwETdKGO1B6hYeZ5nERu7Gs9IgB4q4DPG882IZzm_517VYn5FwOAvTFu0bnY-Ku-2oyDdtbeVua8ZDndh4tbj2W78L2ficnEvGBo7e0ywGiL4rcWdA6Mf5r22NaUsE2OPnKPm0Gv3__hMfpaLTMsmjvDN7Qh73gJFOu4k9JWe2eEYedi0k98_Jj3ZLz6O_6xH9gl_gLYaGt3S-T6sSHIRi72CaFxSD_87-sTUtM7rMm6rcbZoNIHFDpyZPa4q7snS1r3LIaPYFuZ3dfL-ee32_BM8IXzWexkd0jFumJzxhvrXCRiFHyUELMFBlTDLr64gHKRdAu8Qk81mYyiQD1hRqoKovyUVRFvY1oUEaADCLAjNBvMSxMTqksixMtEHCox3ycTBkvOtkMWKgE2jw-NjgDrlCKx_uQTHr9o2y-hn3SxprpazANp1Wcs4nOtE8NakSKByaAB1yyCdcoxhDDuxokv7kAEwVxaviqQQYirrzwiGXwzLGfSzWcSAjPLKlQumQ94dhiCJ8NJIUtrxv70EtNwArDnnVrfphziyMFDgVjKgTfzj5Uacj4LitUvfgqG_-_6NvyaNuGxtfl-Siqe7tO8BBjXbB-dcSrmr22SUPrm6Wq29uu6fgYn4ScF1w5bbB8Rftug2B |
| link.rule.ids | 230,315,733,786,790,870,891,2115,2236,12083,12792,21416,24346,27957,27958,31754,31755,33408,33409,33779,33780,43345,43635,43840,53827,53829,74102,74392,74659 |
| linkProvider | National Library of Medicine |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1Lb9NAEB5BKgQXxLMYCiwSiNPS2PuwfUIpapVCE1WolSoulne9JkZgB9tF5N8zYzshERJXr2WtZ2dn5tvH9wG8trG0kbKGY-pWXIo8JCF3y11oCQPFMtR033k219NL-fFKXQ0Lbs1wrHIdE7tAnVWW1sgPgzCmizeRDt8vf3JSjaLd1UFC4ybsSYFQZQR7R8fz888byCWCTi7NxyzEtYp1f_RdINA_LL79aCidqYC0f7aSUsfd_2-E3kpRu8cnt_LRyT24OxSSbNKP_H244coHcKuXllw9hC_dUh9nv5p37JQ-wGdrIVw2XWV1hY7DSFOYFSWjoPDd_XYNq3I2L9q6Wi7aBVbolk1skTWMVmvZ-aouMNO5R3B5cnzxYcoHHQVulR-13NDWnZBOmLFMhe-ccrGWREXosDyMchEK55tYBplUCMfUOPeFzsI0RzSlDULYxzAqq9I9ARZkARZscWDHVEdJEkzHFJfr1FgCQsaDN2tDJsueLiNBmEEGT7YN7sERWXnzDpFcdw-q-msyzJnERJFTJN_pQinl2KRGZjaLFBGKpgiTPHhLY5TQVEQ72nS4UYBdJVKrZBJieUp89MqDg_UwJsMcbZK_HuXBq00zzi7aMklLV1137xDHG7qPB_v9qG_6LHQcoYNhS7TjDzs_tdtSFouOwdvvAqcWT__fr5dwe3oxO0vOTuefnsEdUrrvjr_FBzBq62v3HOuh1rwYnP4PFN8GHg |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1Lj9MwELZgEYgL4rkEFjASiJNpEz_inFB5lC6w1R5YacXFih2HBkFSkiyi_54ZNy2tkLjGUeSM52mPv4-QZy4TTktnGYRuyQQvUyRyd8ynDmugTKQK7zufzNXsTHw4l-dD_1M3tFVufGJw1EXjcI98lKQZXrzRKh2VQ1vE6dvpq-VPhgxSeNI60GlcJlcwyUY2Az19vy2-eBKI02KIR0zJTK2b4DmU_KPq248OA5tMkAVoJzwFFP9_ffVOsNpvpNyJTNOb5MaQUtLJWgdukUu-vk2urkkmV3fIl7Dpx-iv7iU9xg-wkw0lLp2tirYBFaLILkyrmqJ7-O5_-442JZ1XfdssF_0CcnVHJ64qOor7tvR01VYQ8_xdcjZ99_nNjA2MCszJWPfM4iEeF57bsch57L30mRIISughUdQlT7mPbSaSQkgozOS4jLkq0ryEukpZKGbvkYO6qf19QpMigdQtS9wYMyqB1OkQ7EqVW4clkY3I840gzXINnGGg4ECBm12BR-Q1Snn7DsJdhwdN-9UM1mOs1l4ikadPhRBjm1tRuEJLhBbNoWCKyAtcI4NGCXJ0-XC3AKaK8FZmkkKiisj0MiJHm2U0g7V25q9uReTpdhjsDA9P8to3F-EdRHsD9YnI4XrVt3PmKtOgYDCi9_Rh76f2R-pqEbC84-BCFX_w_3k9IddA282n4_nHh-Q6Ut6HPrjsiBz07YV_BIlRbx8Hjf8DFfII7Q |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Inter-+vs.+Intra-Molecular+Hydrogen+Bond+in+Complexes+of+Nitrophthalic+Acids+with+Pyridine&rft.jtitle=International+journal+of+molecular+sciences&rft.au=J%C3%B3%C5%BAwiak%2C+Kinga&rft.au=Jezierska%2C+Aneta&rft.au=Panek%2C+Jaros%C5%82aw+J&rft.au=Kochel%2C+Andrzej&rft.date=2023-03-09&rft.eissn=1422-0067&rft.volume=24&rft.issue=6&rft_id=info:doi/10.3390%2Fijms24065248&rft_id=info%3Apmid%2F36982321&rft.externalDocID=36982321 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1422-0067&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1422-0067&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1422-0067&client=summon |