Structure and reactivity of o-phthalaldehyde by X-ray, microwave, and molecular orbital calculations
Document Type
Article
Publication Date
1-30-2003
Abstract
Results from a single crystal X-ray diffraction study on o-phthalaldehyde (1) revealed dihedral angles between the CHO groups and the benzene ring of 13(2)° and 27(2)°. In acetaldehyde solution, the 1H-NMR of 1 showed only broadening of the aldehyde singlet down to - 120 °C. The microwave spectrum of 1 was analyzed to give a non-zero second-moment Pcc of 0.662 u-A2, consistent with a non-planar structure in the gas phase with the CHO groups rotated out-of-plane by an average of 10 ± 2°. The X-ray determined structure, microwave experimental results and ab initio calculations at the MP2/6-31 + G(d) level all agree that 1 has a nonplanar structure. There is a remarkable agreement between the structure derived from X-ray and ab initio methods with electron correlation. Ab initio calculations at the Hartree-Fock level optimized to planar structures. © 2002 Elsevier Science B.V. All rights reserved.
Publication Title
Journal of Molecular Structure
Recommended Citation
Mendenhall, G.,
Luck, R.,
Bohn, R.,
&
Castejon, H.
(2003).
Structure and reactivity of o-phthalaldehyde by X-ray, microwave, and molecular orbital calculations.
Journal of Molecular Structure,
645(2-3), 249-258.
http://doi.org/10.1016/S0022-2860(02)00577-X
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/7307