Difference in Energy between Two Distinct Types of Chalcogen Bonds Drives Regioisomerization of Binuclear (Diaminocarbene)Pd II Complexes
The reaction of cis-[PdCl (CNXyl) ] (Xyl = 2,6-Me C H ) with various 1,3-thiazol- and 1,3,4-thiadiazol-2-amines in chloroform gives a mixture of two regioisomeric binuclear diaminocarbene complexes. For 1,3-thiazol-2-amines the isomeric ratio depends on the reaction conditions and kinetically (KRs)...
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| Published in | Journal of the American Chemical Society Vol. 138; no. 42; pp. 14129 - 14137 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
26.10.2016
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| Online Access | Get full text |
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| Abstract | The reaction of cis-[PdCl
(CNXyl)
] (Xyl = 2,6-Me
C
H
) with various 1,3-thiazol- and 1,3,4-thiadiazol-2-amines in chloroform gives a mixture of two regioisomeric binuclear diaminocarbene complexes. For 1,3-thiazol-2-amines the isomeric ratio depends on the reaction conditions and kinetically (KRs) or thermodynamically (TRs) controlled regioisomers were obtained at room temperature and on heating, respectively. In CHCl
solutions, the isomers are subject to reversible isomerization accompanied by the cleavage of Pd-N and C-N bonds in the carbene fragment XylNCN(R)Xyl. Results of DFT calculations followed by the topological analysis of the electron density distribution within the formalism of Bader's theory (AIM method) reveal that in CHCl
solution the relative stability of the regioisomers (ΔG
= 1.2 kcal/mol; ΔG
= 3.2 kcal/mol) is determined by the energy difference between two types of the intramolecular chalcogen bonds, viz. S···Cl in KRs (2.8-3.0 kcal/mol) and S···N in TRs (4.6-5.3 kcal/mol). In the case of the 1,3,4-thiadiazol-2-amines, the regioisomers are formed in approximately equal amounts and, accordingly, the energy difference between these species is only 0.1 kcal/mol in terms of ΔG
(ΔG
= 2.1 kcal/mol). The regioisomers were characterized by elemental analyses (C, H, N), HRESI
-MS and FTIR, 1D (
H,
C{
H}) and 2D (
H,
H-COSY,
H,
H-NOESY,
H,
C-HSQC,
H,
C-HMBC) NMR spectroscopies, and structures of six complexes (three KRs and three TRs) were elucidated by single-crystal X-ray diffraction. |
|---|---|
| AbstractList | The reaction of cis-[PdCl
(CNXyl)
] (Xyl = 2,6-Me
C
H
) with various 1,3-thiazol- and 1,3,4-thiadiazol-2-amines in chloroform gives a mixture of two regioisomeric binuclear diaminocarbene complexes. For 1,3-thiazol-2-amines the isomeric ratio depends on the reaction conditions and kinetically (KRs) or thermodynamically (TRs) controlled regioisomers were obtained at room temperature and on heating, respectively. In CHCl
solutions, the isomers are subject to reversible isomerization accompanied by the cleavage of Pd-N and C-N bonds in the carbene fragment XylNCN(R)Xyl. Results of DFT calculations followed by the topological analysis of the electron density distribution within the formalism of Bader's theory (AIM method) reveal that in CHCl
solution the relative stability of the regioisomers (ΔG
= 1.2 kcal/mol; ΔG
= 3.2 kcal/mol) is determined by the energy difference between two types of the intramolecular chalcogen bonds, viz. S···Cl in KRs (2.8-3.0 kcal/mol) and S···N in TRs (4.6-5.3 kcal/mol). In the case of the 1,3,4-thiadiazol-2-amines, the regioisomers are formed in approximately equal amounts and, accordingly, the energy difference between these species is only 0.1 kcal/mol in terms of ΔG
(ΔG
= 2.1 kcal/mol). The regioisomers were characterized by elemental analyses (C, H, N), HRESI
-MS and FTIR, 1D (
H,
C{
H}) and 2D (
H,
H-COSY,
H,
H-NOESY,
H,
C-HSQC,
H,
C-HMBC) NMR spectroscopies, and structures of six complexes (three KRs and three TRs) were elucidated by single-crystal X-ray diffraction. |
| Author | Boyarskiy, Vadim P. Dar’in, Dmitry V. Kukushkin, Vadim Yu Novikov, Alexander S. Kinzhalov, Mikhail A. Mikherdov, Alexander S. Boyarskaya, Irina A. Starova, Galina L. |
| Author_xml | – sequence: 1 givenname: Alexander S. surname: Mikherdov fullname: Mikherdov, Alexander S. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 2 givenname: Mikhail A. surname: Kinzhalov fullname: Kinzhalov, Mikhail A. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 3 givenname: Alexander S. surname: Novikov fullname: Novikov, Alexander S. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 4 givenname: Vadim P. surname: Boyarskiy fullname: Boyarskiy, Vadim P. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 5 givenname: Irina A. surname: Boyarskaya fullname: Boyarskaya, Irina A. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 6 givenname: Dmitry V. surname: Dar’in fullname: Dar’in, Dmitry V. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 7 givenname: Galina L. surname: Starova fullname: Starova, Galina L. organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation – sequence: 8 givenname: Vadim Yu surname: Kukushkin fullname: Kukushkin, Vadim Yu organization: Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russian Federation |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27700082$$D View this record in MEDLINE/PubMed |
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| Snippet | The reaction of cis-[PdCl
(CNXyl)
] (Xyl = 2,6-Me
C
H
) with various 1,3-thiazol- and 1,3,4-thiadiazol-2-amines in chloroform gives a mixture of two... |
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| Title | Difference in Energy between Two Distinct Types of Chalcogen Bonds Drives Regioisomerization of Binuclear (Diaminocarbene)Pd II Complexes |
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