“Stereoelectronic Deprotection of Nitrogen”: Recovering Nucleophilicity with a Conformational Change
Ureas are often thought of as “double amides” due to the obvious structural similarity of these functional groups. The main structural feature of an amide is its planarity, which is responsible for the conjugation between the nitrogen atom and carbonyl moiety and the decrease of amide nucleophilicit...
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| Published in | Journal of organic chemistry Vol. 88; no. 11; pp. 6868 - 6877 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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American Chemical Society
02.06.2023
Amer Chemical Soc |
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| Abstract | Ureas are often thought of as “double amides” due to the obvious structural similarity of these functional groups. The main structural feature of an amide is its planarity, which is responsible for the conjugation between the nitrogen atom and carbonyl moiety and the decrease of amide nucleophilicity. Consequently, since amides are poor nucleophiles, ureas are often thought of as poor nucleophiles as well. Herein, we demonstrate that ureas can be distinctly different from amides. These differences can be amplified by rotation around one of the ureas’ C–N bonds, which switches off the amide resonance and recovers the nucleophilicity of one of the nitrogen atoms. This conformational change can be further facilitated by the judicious introduction of steric bulk to disfavor the planar conformation. This change in reactivity is an example of “stereoelectronic deprotection,” a concept when the desired reactivity of a functional group is produced by a conformational change rather than a chemical modification. This concept may be used complementarily to the traditional protecting groups. We also demonstrate both the viability and the utility of this concept by the synthesis of unusual 2-oxoimidazolium salts possessing quaternary nitrogen atoms at the urea moiety. |
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| AbstractList | Ureas are often thought of as "double amides" due to the obvious structural similarity of these functional groups. The main structural feature of an amide is its planarity, which is responsible for the conjugation between the nitrogen atom and carbonyl moiety and the decrease of amide nucleophilicity. Consequently, since amides are poor nucleophiles, ureas are often thought of as poor nucleophiles as well. Herein, we demonstrate that ureas can be distinctly different from amides. These differences can be amplified by rotation around one of the ureas' C-N bonds, which switches off the amide resonance and recovers the nucleophilicity of one of the nitrogen atoms. This conformational change can be further facilitated by the judicious introduction of steric bulk to disfavor the planar conformation. This change in reactivity is an example of "stereoelectronic deprotection," a concept when the desired reactivity of a functional group is produced by a conformational change rather than a chemical modification. This concept may be used complementarily to the traditional protecting groups. We also demonstrate both the viability and the utility of this concept by the synthesis of unusual 2-oxoimidazolium salts possessing quaternary nitrogen atoms at the urea moiety.Ureas are often thought of as "double amides" due to the obvious structural similarity of these functional groups. The main structural feature of an amide is its planarity, which is responsible for the conjugation between the nitrogen atom and carbonyl moiety and the decrease of amide nucleophilicity. Consequently, since amides are poor nucleophiles, ureas are often thought of as poor nucleophiles as well. Herein, we demonstrate that ureas can be distinctly different from amides. These differences can be amplified by rotation around one of the ureas' C-N bonds, which switches off the amide resonance and recovers the nucleophilicity of one of the nitrogen atoms. This conformational change can be further facilitated by the judicious introduction of steric bulk to disfavor the planar conformation. This change in reactivity is an example of "stereoelectronic deprotection," a concept when the desired reactivity of a functional group is produced by a conformational change rather than a chemical modification. This concept may be used complementarily to the traditional protecting groups. We also demonstrate both the viability and the utility of this concept by the synthesis of unusual 2-oxoimidazolium salts possessing quaternary nitrogen atoms at the urea moiety. Ureas are often thought of as “double amides” due to the obvious structural similarity of these functional groups. The main structural feature of an amide is its planarity, which is responsible for the conjugation between the nitrogen atom and carbonyl moiety and the decrease of amide nucleophilicity. Consequently, since amides are poor nucleophiles, ureas are often thought of as poor nucleophiles as well. Herein, we demonstrate that ureas can be distinctly different from amides. These differences can be amplified by rotation around one of the ureas’ C–N bonds, which switches off the amide resonance and recovers the nucleophilicity of one of the nitrogen atoms. This conformational change can be further facilitated by the judicious introduction of steric bulk to disfavor the planar conformation. This change in reactivity is an example of “stereoelectronic deprotection,” a concept when the desired reactivity of a functional group is produced by a conformational change rather than a chemical modification. This concept may be used complementarily to the traditional protecting groups. We also demonstrate both the viability and the utility of this concept by the synthesis of unusual 2-oxoimidazolium salts possessing quaternary nitrogen atoms at the urea moiety. Ureas are often thought of as "double amides"dueto the obvious structural similarity of these functional groups. Themain structural feature of an amide is its planarity, which is responsiblefor the conjugation between the nitrogen atom and carbonyl moietyand the decrease of amide nucleophilicity. Consequently, since amidesare poor nucleophiles, ureas are often thought of as poor nucleophilesas well. Herein, we demonstrate that ureas can be distinctly differentfrom amides. These differences can be amplified by rotation aroundone of the ureas' C-N bonds, which switches off theamide resonance and recovers the nucleophilicity of one of the nitrogenatoms. This conformational change can be further facilitated by thejudicious introduction of steric bulk to disfavor the planar conformation.This change in reactivity is an example of "stereoelectronicdeprotection," a concept when the desired reactivity of a functionalgroup is produced by a conformational change rather than a chemicalmodification. This concept may be used complementarily to the traditionalprotecting groups. We also demonstrate both the viability and theutility of this concept by the synthesis of unusual 2-oxoimidazoliumsalts possessing quaternary nitrogen atoms at the urea moiety. |
| Author | Alabugin, Igor V. Burilov, Alexander R. Smolobochkin, Andrey V. Vatsadze, Sergey Z. Sinyashin, Oleg G. Rizbayeva, Tanzilya S. Gazizov, Almir S. |
| AuthorAffiliation | Department of Chemistry and Biochemistry N. D. Zelinsky Institute of Organic Chemistry Arbuzov Institute of Organic and Physical Chemistry |
| AuthorAffiliation_xml | – name: Arbuzov Institute of Organic and Physical Chemistry – name: N. D. Zelinsky Institute of Organic Chemistry – name: Department of Chemistry and Biochemistry |
| Author_xml | – sequence: 1 givenname: Almir S. orcidid: 0000-0001-9899-9606 surname: Gazizov fullname: Gazizov, Almir S. email: agazizov@iopc.ru organization: Arbuzov Institute of Organic and Physical Chemistry – sequence: 2 givenname: Andrey V. orcidid: 0000-0002-1470-8136 surname: Smolobochkin fullname: Smolobochkin, Andrey V. organization: Arbuzov Institute of Organic and Physical Chemistry – sequence: 3 givenname: Tanzilya S. orcidid: 0000-0003-2326-516X surname: Rizbayeva fullname: Rizbayeva, Tanzilya S. organization: Arbuzov Institute of Organic and Physical Chemistry – sequence: 4 givenname: Sergey Z. orcidid: 0000-0001-7884-8579 surname: Vatsadze fullname: Vatsadze, Sergey Z. organization: N. D. Zelinsky Institute of Organic Chemistry – sequence: 5 givenname: Alexander R. surname: Burilov fullname: Burilov, Alexander R. organization: Arbuzov Institute of Organic and Physical Chemistry – sequence: 6 givenname: Oleg G. surname: Sinyashin fullname: Sinyashin, Oleg G. organization: Arbuzov Institute of Organic and Physical Chemistry – sequence: 7 givenname: Igor V. orcidid: 0000-0001-9289-3819 surname: Alabugin fullname: Alabugin, Igor V. organization: Department of Chemistry and Biochemistry |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37216317$$D View this record in MEDLINE/PubMed |
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| Keywords | CATALYSIS ACYCLIC AMIDES DONOR CONSEQUENCES HYDROLYSIS PLANAR BOND DERIVATIVES UREA ACCEPTOR |
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| Snippet | Ureas are often thought of as “double amides” due to the obvious structural similarity of these functional groups. The main structural feature of an amide is... Ureas are often thought of as "double amides"dueto the obvious structural similarity of these functional groups. Themain structural feature of an amide is its... Ureas are often thought of as "double amides" due to the obvious structural similarity of these functional groups. The main structural feature of an amide is... |
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| SubjectTerms | Chemistry Chemistry, Organic Lewis bases moieties nitrogen organic chemistry Physical Sciences Science & Technology urea viability |
| Title | “Stereoelectronic Deprotection of Nitrogen”: Recovering Nucleophilicity with a Conformational Change |
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