Abstract
In our continued quest for novel stable carbenes, silylenes, and germylenes, here we compare and contrast multiplicities and relative stabilities of carbenes affected with four different α-ylides. The latter include carbon, immonium, phosphorus, and sulfur ylides substituted at the alpha positions of carbenes with acyclic, cyclic and cyclicunsaturated structural frameworks. Related thermodynamic data are calculated at B3LYP/6-311++G**//B3LYP/6-31+G* and B3LYP/AUG-cc-pVTZ//B3LYP/6-31+G* levels. Investigations reveal the enlargement of the singlet-triplet energy gaps (ΔΕs-t) in the order of immonium > phosphorus > sulfur > carbon. The observed trend, which is taken as an indication of stability, is thoroughly analyzed by applying appropriate isodesmic reactions which differentiate the substituent effects on each of our singlet or triplet carbene. The effect of unsaturation is also probed in each series of the ylide carbenes. The reactivity of the species is discussed in terms of nucleophilicity and electrophilicity.
Combinatorial Chemistry & High Throughput Screening
Title:Stabilization of Carbenes via α-Ylide Substitutions: A Computational Quest for New Divalents at DFT
Volume: 17 Issue: 8
Author(s): Bibi Narjes Haerizade, Mohammad Zaman Kassaee, Maryam Koohi, Monire Ghavami and Hassan Zandi
Affiliation:
Keywords: A-YHCs, carbene, DFT, NHCs, stability, Ylide.
Abstract: In our continued quest for novel stable carbenes, silylenes, and germylenes, here we compare and contrast multiplicities and relative stabilities of carbenes affected with four different α-ylides. The latter include carbon, immonium, phosphorus, and sulfur ylides substituted at the alpha positions of carbenes with acyclic, cyclic and cyclicunsaturated structural frameworks. Related thermodynamic data are calculated at B3LYP/6-311++G**//B3LYP/6-31+G* and B3LYP/AUG-cc-pVTZ//B3LYP/6-31+G* levels. Investigations reveal the enlargement of the singlet-triplet energy gaps (ΔΕs-t) in the order of immonium > phosphorus > sulfur > carbon. The observed trend, which is taken as an indication of stability, is thoroughly analyzed by applying appropriate isodesmic reactions which differentiate the substituent effects on each of our singlet or triplet carbene. The effect of unsaturation is also probed in each series of the ylide carbenes. The reactivity of the species is discussed in terms of nucleophilicity and electrophilicity.
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Cite this article as:
Haerizade Narjes Bibi, Kassaee Zaman Mohammad, Koohi Maryam, Ghavami Monire and Zandi Hassan, Stabilization of Carbenes via α-Ylide Substitutions: A Computational Quest for New Divalents at DFT, Combinatorial Chemistry & High Throughput Screening 2014; 17 (8) . https://dx.doi.org/10.2174/1386207317666140422155343
DOI https://dx.doi.org/10.2174/1386207317666140422155343 |
Print ISSN 1386-2073 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5402 |
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