Computational Chemical Prediction for the Position of Hydrogen-Deuterium Exchange in Hydroxyindole Derivatives

Takatoshi MATSUMOTOa, Umpei NAGASHIMAa, Kazutoshi TANABEa*, Kimiko HASHIMOTOb, Kazuyo SOGAWAc and Haruhisa SHIRAHAMAc

aNational Institute of Materials and Chemical Research,
Tsukuba, Ibaraki, 305-8565 Japan
bDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University,
3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 Japan
cSchool of Science, Kwansei Gakuin University,
Uegahara Nishinomiya, 662-8501 Japan

(Received: June 9, 1998 ; Accepted for publication: December 9, 1998 ; Published on Web: March 23, 1999)

We report an easy computational procedure for qualitative prediction of hydrogen-deuterium exchange position in hydroxyindole derivatives. The efficiency of the procedure was confirmed with experimental results (Figure 1). Hydrogen-deuterium exchange took place at the carbon atom having the big charge (Figure 3), namely, that next to the hydroxy function. The predicted positions were in good agreement with the observations though there is an exception when steric hindrance should be considered to explain the results.
Atomic charges in basic molecule skeleton obtained by using the molecular orbital calculation enable prediction for the position of hydrogen-deuterium exchange in hydroxy indole derivatives.

Keywords: Hydroxyindole derivatives, Hydrogen-deuterium exchange, Molecular Orbitals, Charge Distribution

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