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Electronic and ligating properties of carbocyclic carbenes: A theoretical investigation
Author(s) -
Bhagat Shweta,
Arfeen Minhajul,
Das Gourav,
Patel Neha,
Bharatam Prasad V.
Publication year - 2019
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.25756
Subject(s) - nucleophile , chemistry , heteroatom , reactivity (psychology) , computational chemistry , dimethylamine , ring (chemistry) , singlet state , proton affinity , ring size , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , ion , physics , alternative medicine , protonation , pathology , nuclear physics , excited state , catalysis
Carbocyclic carbenes (CCCs) are a class of nucleophilic carbenes which are very similar to N ‐heterocyclic carbenes (NHCs) in terms of their reactivity, but they do not contain a stabilizing heteroatom in their cyclic ring system. In this study, 17 representative known CCCs and 34 newly designed CCCs are evaluated using quantum chemical methods, and the results are compared in terms of their stability, nucleophilicity, and proton affinity (PA) parameters. The results are divided on the basis of ring size of the known and reported CCCs. The stability, nucleophilicity, PA, complexation energy, and bond strength–related parameters were estimated using M06/6‐311++G(d,p) method. The results indicated that the CCCs known in the literature are strong σ‐electron donating species and have considerable π‐accepting properties. This study led to the design and identification of a few new CCCs with dimethylamine and diaminomethynyl substituents which can be singlet stable and are substantially nucleophilic. © 2018 Wiley Periodicals, Inc.