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

W. C. Lu; R. Q. Zhang; Q. J. Zang; N. B. Wong

doi:10.1021/jp0146925

Author(s)

W. C. Lu
R. Q. Zhang
Q. J. Zang
N. B. Wong

Related Research Unit(s)

Centre of Super-Diamond and Advanced Films

Detail(s)

Original language	English
Pages (from-to)	2061-2067
Journal / Publication	The Journal of Physical Chemistry B
Volume	107
Issue number	9
Publication status	Published - 6 Mar 2003

Link(s)

DOI	DOI https://doi.org/10.1021/jp0146925 Final Published version
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Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-0037422334&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(27058e12-5244-47fc-b8d4-2deb19943026).html

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)

[ RIS ] [ BibTeX ]

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: The Journal of Physical Chemistry B, Vol. 107, No. 9, 06.03.2003, p. 2061-2067.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

Lu, WC, Zhang, RQ, Zang, QJ & Wong, NB 2003, 'Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction', The Journal of Physical Chemistry B, vol. 107, no. 9, pp. 2061-2067. https://doi.org/10.1021/jp0146925

Lu, W. C., Zhang, R. Q., Zang, Q. J., & Wong, N. B. (2003). Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction. The Journal of Physical Chemistry B, 107(9), 2061-2067. https://doi.org/10.1021/jp0146925

Lu WC, Zhang RQ, Zang QJ, Wong NB. Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction. The Journal of Physical Chemistry B. 2003 Mar 6;107(9):2061-2067. doi: 10.1021/jp0146925

Lu, W. C. ; Zhang, R. Q. ; Zang, Q. J. et al. / Theoretical prediction on efficient formation of imino acid via an aza-Wittig reaction. In: The Journal of Physical Chemistry B. 2003 ; Vol. 107, No. 9. pp. 2061-2067.