Spectra and structure of small ring compounds. LXII. Conformational stability,structural parameters,ab initio calculations and vibrational assignment of cyclopropylmethyl ketone |
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| Institution: | 1. Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, United States;2. Masonic Cancer Center, University of Minnesota, Minneapolis, MN 55455, United States;1. Department of Hepatology, Shenzhen Traditional Chinese Medicine Hospital, The Fourth Clinical Medical College of Guangzhou University of Chinese Medicine, No.1 Fuhua Road, Futian District, Shenzhen, Guangdong 518033, China;2. Guangdong-Hong Kong-Macau Joint Lab on Chinese Medicine and Immune, Disease Research, State Key Laboratory of Dampness Syndrome of Chinese Medicine, Second Affiliated Hospital of Guangzhou University of Chinese Medicine, Guangdong Provincial Hospital of Chinese Medicine, Guangdong Provincial Academy of Chinese Medical Sciences, Guangzhou, Guangdong 510006, China;3. Shenzhen Institute for Drug Control, No. 28, The second Gaoxin Road, Nanshan District, Shenzhen, Guangdong 518000, China;4. Department of Integrated Traditional Chinese and Western Medicine, School of Clinical Medicine, Guangdong Pharmaceutical University, Guangzhou, Guangdong 510006, China |
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| Abstract: | The conformational stability, barriers to internal rotation, and fundamental vibrational frequencies of cyclopropylmethyl ketone, c-C3H5C(CH3)O, have been obtained from Hartree—Fock ab initio calculations with the RHF/3-21G and RHF/6-31G* basis sets, as well as the 6-31G* basis set with electron correlation at the MP2 level, and the results are compared to those obtained from experiment. The data are consistent with the predominant rotamer having the cis conformation (carbonyl bond cis to the ring). A second form, having a “near” trans structure, is calculated to have a larger total dipole moment than the cis form, which accounts for its increased abundance in the liquid compared to that in the gas. A complete vibrational assignment is proposed based on experimental data and normal coordinate results from the ab initio calculations. The asymmetric torsional barrier has been calculated to be approximately 2000 cm?1 and this result along with others is compared to the corresponding data obtained from both experiment and theory for the cyclopropylcarbonyl halides. |
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