A quantum chemical study of the gas-phase homolytic S–Br bond dissociation enthalpies of sulfenyl bromides
作者： Shuaiwei Zhu , Robert J. O'Reilly
DOI: 10.1016/J.CDC.2020.100430
关键词:
摘要: Abstract This study reports the gas-phase homolytic S–Br bond dissociation enthalpies (at 298 K) for a set of 44 sulfenyl bromide derivatives (RSBr) obtained using high-level G4 thermochemical protocol. For species in this set, we find that BDEs range from 178.0 kJ mol–1 (F3CSSBr) to 239.5 (HC(=NH)SBr). We have additionally reported molecule and radical stabilization all species, allowing insights be gained as effect substituents both reactants sulfur-centered products. In addition, also six sufinyl bromides (RS(=O)Br) sulfonyl (RSO2Br). sulfinyl bromides, 156.6 (F3CS(=O)Br) 173.8 (tBuS(=O)Br), whilst 211.0 (F3CSO2Br) 226.2 (FSO2Br).
nu.edu.kz参考文章(25)
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
Angelo. Fontana, Francesco M. Veronese, Ernesto. Scoffone, Sulfenyl halides as modifying reagents for polypeptides and proteins. III. Azobenzene-2-sulfenyl bromide, a selective reagent for cysteinyl residues Biochemistry. ,vol. 7, pp. 3901- 3905 ,(1968) , 10.1021/BI00851A017
Rosana M. Romano, Carlos O. Della Védova, Anthony J. Downs, Tim M. Greene, Matrix Photochemistry of syn-(Chlorocarbonyl)sulfenyl Bromide, syn-ClC(O)SBr: Precursor to the Novel Species anti-ClC(O)SBr, syn-BrC(O)SCl, and BrSCl Journal of the American Chemical Society. ,vol. 123, pp. 5794- 5801 ,(2001) , 10.1021/JA010252F
Nizamuddin Ahmed, Tirtha Bhattacharjee, Pranjit Barman, Saibal Kanti Bhattacharjee, One-Pot, Catalyst-Free, Facile, and Efficient Sulfenylation of Electron-Rich Substrates with a Mild Sulfenium Carrier Azobenzene-2-sulfenyl Bromide Synthetic Communications. ,vol. 43, pp. 2663- 2671 ,(2013) , 10.1080/00397911.2012.733476
Shinzi Kato, Kenji Miyagawa, Satoshi Kawabata, Masaru Ishida, A Convenient Preparation of Acylsulfenyl Bromides: A New Class of Electrophilic Thiocarboxylating Agents Synthesis. ,vol. 1982, pp. 1013- 1014 ,(1982) , 10.1055/S-1982-30042
Michael W. Schmidt, Kim K. Baldridge, Jerry A. Boatz, Steven T. Elbert, Mark S. Gordon, Jan H. Jensen, Shiro Koseki, Nikita Matsunaga, Kiet A. Nguyen, Shujun Su, Theresa L. Windus, Michel Dupuis, John A. Montgomery, General atomic and molecular electronic structure system Journal of Computational Chemistry. ,vol. 14, pp. 1347- 1363 ,(1993) , 10.1002/JCC.540141112
Mateusz Szymelfejnik, Janusz Rachon, Sebastian Demkowicz, Dariusz Witt, The Organophosphorus Sulfenyl Bromides as Versatile Reagents for Cysteine Derivatives Functionalization by Unsymmetrical Disulfide Bond Formation Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 183, pp. 415- 419 ,(2008) , 10.1080/10426500701735437
Yeny A. Tobón, Laura I. Nieto, Rosana M. Romano, Carlos O. Della Védova, Anthony J. Downs, Photochemical Reaction Channels of OCS with Cl2, ICl, or IBr Isolated Together in an Argon Matrix: Isolation ofsyn-Iodocarbonylsulfenyl Bromide The Journal of Physical Chemistry A. ,vol. 110, pp. 2674- 2681 ,(2006) , 10.1021/JP056135E
Jing Tan, Fushun Liang, Yeming Wang, Xin Cheng, Qun Liu, Hongjuan Yuan, Carbon tetrabromide-mediated carbon-sulfur bond formation via a sulfenyl bromide intermediate. Organic Letters. ,vol. 10, pp. 2485- 2488 ,(2008) , 10.1021/OL800765S