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Information Journal Paper

Title

HYBRID-DFT STUDY AND NBO INTERPRETATION OF CONFORMATIONAL ANALYSIS OF DIHYDROXYMETHANE IN RELATION TO THE ANOMERIC EFFECT

Pages

  101-108

Abstract

 Introduction: The conformational behavior of DIHYDROXYMETHANE has been analyzed by means of hybrid-density functional theory (B3LYP/6-311++G**) based method and NBO interpretation.Aim: The correlation between the energy differences between the various conformations of DIHYDROXYMETHANE, the anomeric effect associated with the electron delocalization, diploe-dipole interactions (i.e. the electrostatic mode) and steric repulsions have been investigated. Results: Based on the potential energy surface obtained at the B3LYP/6-311++G** level of theory, the most stable conformation of DIHYDROXYMETHANE is found to be an axial symmetrical (C2 symmetry) conformation (i.e. gauche-gauche, g.g). The calculated energy for the second lowest energy-minimum conformation, viz. gauche-gauche* (g.g*, Cs symmetry) is 2.44 kcal mol-1. Third lowest energy-minimum structure of DIHYDROXYMETHANE is the unsymmetrical quasi-gauche-anti conformation (i.e. qa.g, by about 2.58 kcal mol-1 higher than g.g conformation). Based on the obtained NBO results, the calculated GENERALIZED ANOMERIC EFFECT (GAE) value decreases from of the g.g conformation of DIHYDROXYMETHANE to its qa.g conformation but decreases from qa.g conformation to g.g* conformation. Therefore, the GAE can not explain the more stability of the g.g conformation of DIHYDROXYMETHANE compared to the corresponding g.g* conformation. On the other hand, the calculated dipole moment value of the g.g conformation of DIHYDROXYMETHANE is smaller than that of g.g* conformation.Conclusion: Interestingly, these findings led to the proposal that the electrostatic model is more significant for the explanation of the conformational preference of DIHYDROXYMETHANE than the GAE and steric interactions.

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    APA: Copy

    MOEINZADEH, R., NORI SHARGH, D., YAHYAEI, H., NEJAD REZAEI, L., CHALEHCHALEH, N., & MADHI TAZEHKAND, A.. (2011). HYBRID-DFT STUDY AND NBO INTERPRETATION OF CONFORMATIONAL ANALYSIS OF DIHYDROXYMETHANE IN RELATION TO THE ANOMERIC EFFECT. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), 21(80 (CHEMISTRY ISSUE)), 101-108. SID. https://sid.ir/paper/617205/en

    Vancouver: Copy

    MOEINZADEH R., NORI SHARGH D., YAHYAEI H., NEJAD REZAEI L., CHALEHCHALEH N., MADHI TAZEHKAND A.. HYBRID-DFT STUDY AND NBO INTERPRETATION OF CONFORMATIONAL ANALYSIS OF DIHYDROXYMETHANE IN RELATION TO THE ANOMERIC EFFECT. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY)[Internet]. 2011;21(80 (CHEMISTRY ISSUE)):101-108. Available from: https://sid.ir/paper/617205/en

    IEEE: Copy

    R. MOEINZADEH, D. NORI SHARGH, H. YAHYAEI, L. NEJAD REZAEI, N. CHALEHCHALEH, and A. MADHI TAZEHKAND, “HYBRID-DFT STUDY AND NBO INTERPRETATION OF CONFORMATIONAL ANALYSIS OF DIHYDROXYMETHANE IN RELATION TO THE ANOMERIC EFFECT,” JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), vol. 21, no. 80 (CHEMISTRY ISSUE), pp. 101–108, 2011, [Online]. Available: https://sid.ir/paper/617205/en

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