Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

Detail(s)

Original languageEnglish
Pages (from-to)2061-2067
Journal / PublicationJournal of Physical Chemistry B
Volume107
Issue number9
Publication statusPublished - 6 Mar 2003

Abstract

An intermolecular aza-Wittig reaction Ph3PNH + OHCCOOH → Ph3PO + NHCHCOOH has been studied theoretically using ab initio calculations at the MP2/6-31G*//HF/6-31G* level of theory. We find that the aza-Wittig reaction used to form iminoacetic acid (NHCHCOOH) from (E)/(Z)-glyoxalic acid (OHCCOOH) involves low energy barriers (the two dominant barriers are 4.5/6.7 and 22.0/17.6 kcal/mol, respectively) and is exothermic (23.8/29.3 kcal/mol). We conjecture that the ease of the intermolecular aza-Wittig reaction could provide a new and efficient way of synthesizing imino acids.

Citation Format(s)

Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction. / Lu, W. C.; Zhang, R. Q.; Zang, Q. J. et al.
In: Journal of Physical Chemistry B, Vol. 107, No. 9, 06.03.2003, p. 2061-2067.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review