A study of conformational stability and vibrational assignments of 1-aminocyclopropanecarboxylic acid c-C3H4(NH2)-COOH.
作者： Hassan M. Badawi
DOI: 10.1016/J.SAA.2009.03.014
关键词:
摘要: The structural stability of 1-aminocyclopropanecarboxylic acid was investigated at DFT-BLYP, DFT-B3LYP and ab initio MP2 levels theory with 6-311G(**) basis set. molecule predicted the three calculation to exist in cis-syn trans-syn conformational equilibrium. equilibrium constants for interconversion were calculated found correspond an mixture about 35% 65% conformations 298.15 K. cis-trans rotational barrier NH(2)syn-anti inversion estimated be 6 7 kcal/mol, respectively. O-H order 12-14 kcal/mol. vibrational frequencies two stable conformers computed BLYP B3LYP theory. Only assignments provided low energy conformer on normal coordinate analysis experimental data. No clear evidence presence second high structure spectra molecule.
elsevier.com
sci-hub.se 参考文章(12)
G. Nowak, Y. Li, I. A. Paul, Chronic glycine treatment desensitizes the behavioral response to 1-aminocyclopropanecarboxylic acid (ACPC), a partial agonist at the strychnine-insensitive glycine site of the NMDA receptor complex. Journal of Neural Transmission. ,vol. 107, pp. 123- 131 ,(2000) , 10.1007/S007020050011
Farina Brackmann, Armin de Meijere, Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids Chemical Reviews. ,vol. 107, pp. 4493- 4537 ,(2007) , 10.1021/CR078376J
Hassan M. Badawi, Wolfgang F�rner, Theoretical vibrational spectra of cyclohexanecarboxaldehyde Journal of Molecular Modeling. ,vol. 7, pp. 288- 305 ,(2001) , 10.1007/S008940100016
K.-M. Marstokk, Harald Møllendal, Svein Samdal, Stephen Cradock, David W. H. Rankin, Svante Wold, George W. Francis, Britt Karlsson, The Structure of Gaseous Cyclopropanecarboxylic Acid as Studied by Microwave Spectroscopy, Electron Diffraction and Ab Initio Calculations Acta Chemica Scandinavica. ,vol. 45, pp. 37- 45 ,(1991) , 10.3891/ACTA.CHEM.SCAND.45-0037
H.M. Badawi, A.A. Al-Saadi, M.A.A. Al-Khaldi, S.A. Al-Abbad, Z.H.A. Al-Sunaidi, Potential energy scans and vibrational assignments of cyclopropanecarboxylic acid and cyclopropanecarboxamide. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 71, pp. 1540- 1546 ,(2008) , 10.1016/J.SAA.2008.05.018
Jesus Gomez-Catalan, Carlos Aleman, Juan J. Perez, Conformational profile of 1-aminocyclopropanecarboxylic acid Theoretical Chemistry Accounts. ,vol. 103, pp. 380- 389 ,(2000) , 10.1007/S002149900066
Ming GAO, Fumio KONDO, Takayasu MURAKAMI, Jin-Wen XU, Ning MA, Xuxiang ZHU, Kazu MORI, Torao ISHIDA, 1-Aminocyclopropanecarboxylic Acid, an Antagonist of N-Methyl-D-Aspartate Receptors, Causes Hypotensive and Antioxidant Effects with Upregulation of Heme Oxygenase-1 in Stroke- Prone Spontaneously Hypertensive Rats Hypertension Research. ,vol. 30, pp. 249- 257 ,(2007) , 10.1291/HYPRES.30.249
D.L. Powell, P. Klaboe, Conformational behaviour and vibrational spectra of cyclopropanecarboxylic acid and cyclopropanecarboxamide Journal of Molecular Structure. ,vol. 15, pp. 217- 223 ,(1973) , 10.1016/0022-2860(73)85005-7
Yu Lin, Joseph B Long, Prolonged pre-exposure to 1-aminocyclopropanecarboxylic acid protects against subsequent glutamate toxicity in vitro European Journal of Pharmacology. ,vol. 338, pp. 289- 292 ,(1997) , 10.1016/S0014-2999(97)81932-2
Steven L Peterson, Rebecca S Purvis, James W Griffith, Differential neuroprotective effects of the NMDA receptor-associated glycine site partial agonists 1-aminocyclopropanecarboxylic acid (ACPC) and D-cycloserine in lithium-pilocarpine status epilepticus. Neurotoxicology. ,vol. 25, pp. 835- 847 ,(2004) , 10.1016/J.NEURO.2004.01.003