An Ab Initio Theory and Density Functional Theory (DFT) Study of Conformers of Tetrahydro-2H-Pyran
Document Type
Article
Publication Date
11-8-2001
Abstract
Ab initio theory with the 3-21G, 6-31G(d), 6-31G(d,p), 6-311G(d,p), 6-31+G(d), and 6-311+G(d,p) basis sets and density functional theory (SVWN, pBP, BLYP), including the hybrid density functional methods B3LYP, B3PW91, and B3P86, have been used to calculate the energies of the chair, half-chair, sofa, twist, and boat conformers of tetrahydro-2H-pyran (oxacyclohexane, oxane, pentamethylene oxide, tetrahydropyran, THP). The enthalpies (ΔH°), entropies (ΔS°), and free energies (ΔG°) of the conformers were also determined. The energy difference (°E, kcal/mol) between the chair and the 2,5-twist conformer is 5.92 to 6.10 (HF), 5.78 to 6.10 (MP2), 6.71 to 6.82 (SVWN), 6.04 to 6.12 (pBP), and 5.84 to 5.95 (BLYP, B3LYP, B3PW91, B3P86). The energy difference (°E, kcal/mol) between the chair and the 1,4-boat conformer is 6.72 to 7.05 (HF), 6.76 to 7.16 (MP2), 6.97 to 7.20 (SVWN), 6.26 to 6.36 (pBP), and 6.23 to 6.46 (BLYP, B3LYP, B3PW91, B3P86). The transition state between the chair conformation and the 2,5-twist conformation is 11 kcal/mol higher in energy than the chair conformer.
DOI
10.1021/jp012342c
Montclair State University Digital Commons Citation
Freeman, Fillmore; Kasner, Marc; and Hehre, Warren J., "An Ab Initio Theory and Density Functional Theory (DFT) Study of Conformers of Tetrahydro-2H-Pyran" (2001). Department of Chemistry and Biochemistry Faculty Scholarship and Creative Works. 65.
https://digitalcommons.montclair.edu/chem-biochem-facpubs/65