A study of conformational stability and vibrational assignments of 1-aminocyclopropanecarboxylic acid c-C3H4(NH2)-COOH

Hassan M. Badawi

doi:10.1016/j.saa.2009.03.014

A study of conformational stability and vibrational assignments of 1-aminocyclopropanecarboxylic acid c-C₃H₄(NH₂)-COOH

Hassan M. Badawi^*

^*Corresponding author for this work

King Fahd University of Petroleum & Minerals

Research output: Contribution to journal › Article › peer-review

Abstract

The structural stability of 1-aminocyclopropanecarboxylic acid was investigated at DFT-BLYP, DFT-B3LYP and ab initio MP2 levels of theory with 6-311G^** basis set. The molecule was predicted at the three levels of calculation to exist in cis-syn ⇔ trans-syn conformational equilibrium. The equilibrium constants for the conformational interconversion were calculated and found to correspond to an equilibrium mixture of about 35% cis-syn and 65% trans-syn conformations at 298.15 K. The cis-trans rotational barrier and the NH₂ syn-anti inversion barrier were estimated to be about 6 and 7 kcal/mol, respectively. The O-H rotational barrier was calculated to be of the order 12-14 kcal/mol. The vibrational frequencies of the two stable conformers of the acid were computed at the BLYP and the B3LYP levels of theory. Only vibrational assignments were provided for the low energy trans-syn conformer on the basis of normal coordinate analysis and experimental data. No clear evidence was found for the presence of the second high energy cis-syn structure in the spectra of the molecule.

Original language	English
Pages (from-to)	707-712
Number of pages	6
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	73
Issue number	4
DOIs	https://doi.org/10.1016/j.saa.2009.03.014
State	Published - 15 Aug 2009

Bibliographical note

Funding Information:
The author gratefully acknowledges the support of this work by King Fahd University of Petroleum and Minerals. The author also greatly appreciates the free access to infrared spectra provided by SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (National Institute of Advanced Industrial Science and Technology, 2008); SDBS No. 16052.

Keywords

1-Aminocyclopropanecarboxylic acid
Conformational equilibrium constant
Vibrational spectra and assignments

ASJC Scopus subject areas

Analytical Chemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Spectroscopy

Access to Document

10.1016/j.saa.2009.03.014

Cite this

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title = "A study of conformational stability and vibrational assignments of 1-aminocyclopropanecarboxylic acid c-C3H4(NH2)-COOH",

abstract = "The structural stability of 1-aminocyclopropanecarboxylic acid was investigated at DFT-BLYP, DFT-B3LYP and ab initio MP2 levels of theory with 6-311G** basis set. The molecule was predicted at the three levels of calculation to exist in cis-syn ⇔ trans-syn conformational equilibrium. The equilibrium constants for the conformational interconversion were calculated and found to correspond to an equilibrium mixture of about 35\% cis-syn and 65\% trans-syn conformations at 298.15 K. The cis-trans rotational barrier and the NH2 syn-anti inversion barrier were estimated to be about 6 and 7 kcal/mol, respectively. The O-H rotational barrier was calculated to be of the order 12-14 kcal/mol. The vibrational frequencies of the two stable conformers of the acid were computed at the BLYP and the B3LYP levels of theory. Only vibrational assignments were provided for the low energy trans-syn conformer on the basis of normal coordinate analysis and experimental data. No clear evidence was found for the presence of the second high energy cis-syn structure in the spectra of the molecule.",

keywords = "1-Aminocyclopropanecarboxylic acid, Conformational equilibrium constant, Vibrational spectra and assignments",

author = "Badawi, \{Hassan M.\}",

note = "Funding Information: The author gratefully acknowledges the support of this work by King Fahd University of Petroleum and Minerals. The author also greatly appreciates the free access to infrared spectra provided by SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (National Institute of Advanced Industrial Science and Technology, 2008); SDBS No. 16052. ",

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PY - 2009/8/15

Y1 - 2009/8/15

N2 - The structural stability of 1-aminocyclopropanecarboxylic acid was investigated at DFT-BLYP, DFT-B3LYP and ab initio MP2 levels of theory with 6-311G** basis set. The molecule was predicted at the three levels of calculation to exist in cis-syn ⇔ trans-syn conformational equilibrium. The equilibrium constants for the conformational interconversion were calculated and found to correspond to an equilibrium mixture of about 35% cis-syn and 65% trans-syn conformations at 298.15 K. The cis-trans rotational barrier and the NH2 syn-anti inversion barrier were estimated to be about 6 and 7 kcal/mol, respectively. The O-H rotational barrier was calculated to be of the order 12-14 kcal/mol. The vibrational frequencies of the two stable conformers of the acid were computed at the BLYP and the B3LYP levels of theory. Only vibrational assignments were provided for the low energy trans-syn conformer on the basis of normal coordinate analysis and experimental data. No clear evidence was found for the presence of the second high energy cis-syn structure in the spectra of the molecule.

AB - The structural stability of 1-aminocyclopropanecarboxylic acid was investigated at DFT-BLYP, DFT-B3LYP and ab initio MP2 levels of theory with 6-311G** basis set. The molecule was predicted at the three levels of calculation to exist in cis-syn ⇔ trans-syn conformational equilibrium. The equilibrium constants for the conformational interconversion were calculated and found to correspond to an equilibrium mixture of about 35% cis-syn and 65% trans-syn conformations at 298.15 K. The cis-trans rotational barrier and the NH2 syn-anti inversion barrier were estimated to be about 6 and 7 kcal/mol, respectively. The O-H rotational barrier was calculated to be of the order 12-14 kcal/mol. The vibrational frequencies of the two stable conformers of the acid were computed at the BLYP and the B3LYP levels of theory. Only vibrational assignments were provided for the low energy trans-syn conformer on the basis of normal coordinate analysis and experimental data. No clear evidence was found for the presence of the second high energy cis-syn structure in the spectra of the molecule.

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