IIIT Hyderabad Publications |
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Some theoretical insights into preferential mode of cyclization in tetrahydrofuran amino acidsAuthors: N. V. Suresh Kumar,Purshotam Sharma,Tushar Kanti Chakraborty,Harjinder Singh Conference: Discussion meeting on Theoretical Chemistry (TCS-2009), Bangalore, January 18-22, 2009. Date: 2009-09-01 Report no: IIIT/TR/2009/113 AbstractWe provide theoretical insights for the observed preference of cyclodimerization over intramolecular cyclization reactions in tetrahydrofuran amino acid using high level ab initio quantum chemical methods,1,2 including detailed analysis of the geometrical, energetic and thermodynamic analysis aspects governing the feasibility of these reactions in the gas phase as well as in continuum solvent medium. Thermodynamic results obtained from Hessian calculations indicate the higher stability of intermolecularly cyclized dimer over intramolecularly cyclized monomer. Geometrical analysis performed on the cyclized products shows the possibility of the presence of hydrogen bonding interaction in intermolecularly cyclized products. NBO and AIM analysis also support the existence of additional stabilizing hydrogen bond interaction in intermolecularly cyclized products. References: 1. H. Singh, K. Arora, S. Tapadar, T. K. Chakraborty J. Theor. Comput. Chem. (2004) 3:55-566. 2. M. Sharma, P. Kumar,, H. Singh, T. K. Chakraborty J. Mol. Struct. THEOCHEM (2006) 764:109-115. Centre for Computational Natural Sciences and Bioinformatics |
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