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Quantum-Chemical Estimate of Dipole Moments of Tropones and Tropolones

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Abstract

Data on the experimental dipole moments of tropones and tropolones including natural compounds and their substitution products and analogs were systematized. Dipole moments (μ) of 28 tropones and 34 tropolones were calculated using MNDO, AM1, and PM3. The capabilities of these bonding schemes to estimate the μ values were found. Correlations μexp = bμtheor were found. The electronic structure of parent molecules of these compounds was studied using the ab initio (RHF/6-31G **) method. It has been found that the regioselectivity of electrophilic reactions of troponoids is consistent with the distribution of electron density in the molecules that was found using semi-empirical MNDO, AM1, PM3 and ab initio methods.

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  1. N. G. Chernyshevskii Saratov State University, 410012, Saratov, ul. Astrakhanskaya, 83

    A. N. Pankratov

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Pankratov, A.N. Quantum-Chemical Estimate of Dipole Moments of Tropones and Tropolones. Chemistry of Natural Compounds 39, 553–562 (2003). https://doi.org/10.1023/B:CONC.0000018109.29629.6a

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