The influence of halogen bonds on tautomerism: the case of 3-mercapto-1,2-azoles (pyrazoles, isoxazoles, isothiazoles)
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- 作者：Marta Marín-Luna ; Ibon Alkorta ; José Elguero
- 关键词：Tautomerism ; Halogen bonds ; Molecular electrostatic potentials ; Binding energies ; Stabilizing charge ; transfer energies
- 刊名：Structural Chemistry
- 出版年：2015
- 出版时间：June 2015
- 年：2015
- 卷：26
- 期：3
- 页码：639-645
- 全文大小：635 KB
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Ibon Alkorta (1)
José Elguero (1)
1. Instituto de Química Médica (CSIC), Juan de la Cierva, 3, 28006, Madrid, Spain
2. Murcia, Spain - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Computer Applications in Chemistry
Physical Chemistry
Theoretical and Computational Chemistry - 出版者：Springer Netherlands
- ISSN：1572-9001
文摘
DFT calculations at the B3LYP/6-311++G(d,p) computational level have been carried out on three tautomeric pairs of 3-mercapto-1,2-azoles (pyrazoles, isoxazoles, and isothiazoles) to study the effect of halogen bonds (XBs) on the position of the equilibrium. As halogen bond donors, we have selected Br2, Cl2, BrCl, ClF and BrF and compare them with HF as a hydrogen bond donor. Several linear relationships were found between binding energies of different halogen bond donors. The main conclusion of this study is that the XB inverts the tautomeric equilibrium while an HB does not.