Homolytic C–Br bond dissociation energies obtained by means of the G4 thermochemical protocol
作者： Zhanna Kazakbayeva , Shingis Zhumagali , Abdulla Mahboob , Robert J. O'Reilly
DOI: 10.1016/J.CDC.2016.04.002
关键词: Organic molecules 、 Nucleobase 、 Chemical diversity 、 Bond cleavage 、 Chemistry 、 Computational chemistry 、 Bond-dissociation energy 、 Structural diversity 、 Radical 、 Stereochemistry 、 Homolysis
摘要: Abstract Knowledge of the energies required to induce homolytic cleavage C–Br bonds brominated organic molecules, a process that affords carbon-centered radicals and Br • , is fundamental importance. Although some data pertaining strength can already be found in literature, chemical diversity species for which bond dissociation (BDEs) are available somewhat limited. In this article, we report comprehensive set BDEs, obtained using G4 thermochemical protocol, molecules with wide structural diversity. The have BDEs (at 298 K) differ by as much 188.3 kJ mol –1 α-bromoalanine having lowest BDE (214.1 kJ mol ) 1-bromobut-1-yne largest (402.4 kJ mol ). Of particular relevance biological systems 8-bromoguanine (345.3 kJ mol ), 8-bromoadenine (345.6 kJ mol 5-bromocytosine (348.8 kJ mol 5-bromouracil (350.3 kJ mol
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J.H. Boyer, R. Selvarajan, Photolysis of vic-triazoles. Tetrahedron Letters. ,vol. 10, pp. 47- 50 ,(1969) , 10.1016/S0040-4039(01)97649-X
Yu-Ran Luo, Comprehensive handbook of chemical bond energies ,(2007)
Igor Ying Zhang, Jianming Wu, Yi Luo, Xin Xu, None, Trends in R-X Bond Dissociation Energies (R(•) = Me, Et, i-Pr, t-Bu, X(•) = H, Me, Cl, OH). Journal of Chemical Theory and Computation. ,vol. 6, pp. 1462- 1469 ,(2010) , 10.1021/CT100010D
Robert J. O'Reilly, Amir Karton, A dataset of highly accurate homolytic NBr bond dissociation energies obtained by Means of W2 theory International Journal of Quantum Chemistry. ,vol. 116, pp. 52- 60 ,(2016) , 10.1002/QUA.25024
Xiao-Hong Li, Rui-Zhou Zhang, Xin-Lu Cheng, Xiang-Dong Yang, PCM study of the solvent and substituent effects on bond dissociation energies in O-nitrosyl carboxylate compounds Journal of Molecular Structure: THEOCHEM. ,vol. 821, pp. 47- 52 ,(2007) , 10.1016/J.THEOCHEM.2007.06.026
Khaled Othmen, Pierre Boule, Claire Richard, Mechanism of 3-halogenoaniline photolysis in methanol New Journal of Chemistry. ,vol. 23, pp. 857- 861 ,(1999) , 10.1039/A902609F
P. Bosch, F. del Monte, J.L. Mateo, R.S. Davidson, New cleavage photoinitiators for radical polymerization: synthesis and photochemical study of dibromo derivatives of dibenzoylmethane Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 73, pp. 197- 204 ,(1993) , 10.1016/1010-6030(93)90005-6
Michelle L. Coote, Addy Pross, Leo Radom, Variable Trends in R-X Bond Dissociation Energies (R = Me, Et, i -Pr, t -Bu) Organic Letters. ,vol. 5, pp. 4689- 4692 ,(2003) , 10.1021/OL035860+
Jarugu Narasimha Moorthy, Subhas Samanta, Photoinduced C-Br homolysis of 2-bromobenzophenones and Pschorr ring closure of 2-aroylaryl radicals to fluorenones. Journal of Organic Chemistry. ,vol. 72, pp. 9786- 9789 ,(2007) , 10.1021/JO7017872
Konstantin Yu. Amsharov, Martin Jansen, C48 Buckybowl and C60 Fullerene Precursors on the Basis of Truxenone Zeitschrift für Naturforschung B. ,vol. 62, pp. 1497- 1508 ,(2007) , 10.1515/ZNB-2007-1206