Study of Electronic Effects on Normal vs. Abnormal Tetrazol-5-ylidenes at DFT

Document Type: Research Article

Authors

1 Associate Professor of Organic Chemistry Tarbiat Modares University

2 Organic chemistry,Tarbiat Modares,Tehran,Iran

Abstract

We present electronic effects on stability (ΔES-T), nucleophilicity (N), global electrophilicity (ω), and band gaps (ΔEHOMO-LUMO) of 36 novel 1,4- and 1,3-tetrazole-5-ylidenes, 1 and 2, respectively. A union of three sets of "normal" 1W,W, 1D,D, and 1D,W are compared to another union of four sets of "abnormal" 2W,W, 2D,D, 2D,W and 2W,D NHCs, electron withdrawing substituents (W) and electron donating ones (D). Every 1 is more stable and shows a larger band gap than its corresponding 2. In addition, philicities, N and ω, of every 2 appear larger than that of the corresponding 1 isomer. Carbenes with W groups in-crease electrophilicity while D ones increase nucleophilicity and in pull-push groups, W group in car-bene center increase electrophilicity. All our NHCs give doubly bonded head-to-head dimers except for 5 species.

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