Potential energy scans and vibrational assignments of cyclopropanecarboxylic acid and cyclopropanecarboxamide.
作者： H.M. Badawi , A.A. Al-Saadi , M.A.A. Al-Khaldi , S.A. Al-Abbad , Z.H.A. Al-Sunaidi
DOI: 10.1016/J.SAA.2008.05.018
关键词: Equilibrium constant 、 Ab initio 、 Conformational isomerism 、 Potential energy 、 Crystallography 、 Molecule 、 Chemistry 、 Computational chemistry 、 Ring (chemistry) 、 Amide 、 Cyclopropane
摘要: Abstract The structural stability and internal rotations in cyclopropanecarboxylic acid cyclopropanecarboxamide were investigated by the DFT-B3LYP ab initio MP2 calculations using 6-311G** 6-311+G** basis sets. computations extended to MP4//MP2/6-311G** CCSD(T)//MP2/6-311G** single-point calculations. From molecules predicted exist predominantly cis (C O group eclipses cyclopropane ring) with a – trans barrier of about 4–6 kcal/mol. OCOH torsional was estimated be 12–13 kcal/mol while corresponding OCNH amide calculated 20 kcal/mol. equilibrium constant k for ⇔ interconversion 0.1729 at 298.15 K that corresponds an mixture 85% 15% . vibrational frequencies computed level. Normal coordinate carried out potential energy distributions low conformer molecules. Complete assignments made on normal comparison experimental data
harvard.edu
elsevier.com
sci-hub.se 参考文章(21)
Hassan M. Badawi, Wolfgang F�rner, Ali A. Al-Rayyes, An Investigation of Structural Stability and Internal Rotation in 3-Cyclopropenecarboxaldehyde and 3-Cyclopropenecarboxylic Acid Fluoride by ab initio Calculations Journal of Molecular Modeling. ,vol. 4, pp. 158- 164 ,(1998) , 10.1007/S0089480040158
Hassan M. Badawi, Wolfgang F�rner, Theoretical vibrational spectra of cyclohexanecarboxaldehyde Journal of Molecular Modeling. ,vol. 7, pp. 288- 305 ,(2001) , 10.1007/S008940100016
Hassan M. Badawi, Effect of bulk groups substitution on conformational behavior and structure of gauche-gauche cyclopropylmethanol Journal of Molecular Structure: THEOCHEM. ,vol. 288, pp. 93- 103 ,(1993) , 10.1016/0166-1280(93)90098-V
Vlado Tabacik, Jacques Maillols, Vibrational spectra in cyclopropane series—III. Fundamental modes of cyclopropanecarboxylic acid monomer and of its -OD species Spectrochimica Acta Part A: Molecular Spectroscopy. ,vol. 34, pp. 315- 329 ,(1978) , 10.1016/0584-8539(78)80153-6
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
J. R. Durig, Fusheng Feng, T. S. Little, Ai -Ying Wang, Conformational stability, barriers to internal rotation, structural parameters, ab initio calculations, and vibrational assignment of cyclopropanecarboxaldehyde Structural Chemistry. ,vol. 3, pp. 417- 428 ,(1992) , 10.1007/BF00672016
H.M. Badawi, M.A.A. Al-Khaldi, S.S.A. Al-Abbad, Z.H.A. Al-Sunaidi, Rotational barriers in monomeric CH2=CX-COOH and CH2=CX-CONH2 (X is H or CH3) and vibrational analysis of methacrylic acid and methacrylamide. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 68, pp. 432- 442 ,(2007) , 10.1016/J.SAA.2006.11.048
J.R. Durig, Ai-Ying Wang, T.S. Little, Far-infrared spectrum, barriers to internal rotation, structural parameters, and vibrational assignment of cyclopropylcarbonyl fluoride Journal of Molecular Structure. ,vol. 244, pp. 117- 137 ,(1991) , 10.1016/0022-2860(91)80152-T
Hassan M. Badawi, Conformational equilibria and structure of cyclopropylcarboxaldehyde and 1-methyl and 1-halo derivatives Journal of Molecular Structure-theochem. ,vol. 228, pp. 159- 165 ,(1991) , 10.1016/0166-1280(91)90053-M
H.M Badawi, Goran Baranovic, P Groner, Mengzhang Zhen, J.R Durig, Raman spectra, conformational stability, structural parameters, vibrational assignment, and ab initio calculations for epifluorohydrin Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 50, pp. 383- 397 ,(1994) , 10.1016/0584-8539(94)80156-8