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Theoretical investigation of Banert cascade reaction.

ABSTRACT: Computational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2'-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is much faster than SN2' displacement in the order of 8. The [3,3]-sigmatropic rearrangement for the conversion of propargyl azide into triazafulvene has been proved as the rate-determining step having highest activation energy parameter. Solvent effect on total course of reaction has been found negligible. Furthermore, effects of different density functional theory functionals and functional groups on activation energies of [3,3]-sigmatropic rearrangement of propargyl azide were also studied. BHHLYP, ?B97XD, M062X and BMK calculated ?G‡ are consistent with B3LYP.

SUBMITTER: Bhattacharyya S

PROVIDER: S-EPMC5936888 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Theoretical investigation of Banert cascade reaction.

Bhattacharyya S S Hatua K K

Royal Society open science 20180404 4

Computational inside of Banert cascade reaction for triazole formation is studied with B3LYP/6-31G(d,p) level of theory. The reaction proceeds mainly by SN2 initial chloride displacement rather than SN2'-type attack. Furthermore, according to the rate of reaction calculation, SN2 displacement is much faster than SN2' displacement in the order of 8. The [3,3]-sigmatropic rearrangement for the conversion of propargyl azide into triazafulvene has been proved as the rate-determining step having high ...[more]

PMID: 29765623

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