Crystal structure and feasibility of intramolecular proton transfer reaction of salicylaldazine

Mijanuddin, Md. ; Sheldrick, W. S. ; Mayer-Figge, H. ; Ali, Mahammad ; Chattopadhyay, Nitin (2004) Crystal structure and feasibility of intramolecular proton transfer reaction of salicylaldazine Journal of Molecular Structure, 693 (1-3). pp. 161-165. ISSN 0022-2860

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.molstruc.2004.02.030

Abstract

The work describes characterization of salicylaldazine by IR, NMR and single crystal X-ray diffraction studies. The compound crystallizes in the monoclinic crystal system with the space group P21/n, a=8.554(3), b=6.338(2), c=11.864(5) Å, and β=107.89(2)°. There are two strong intramolecular hydrogen bonds of the type O-H...N and two weak hydrogen bridges of the type C-H...O which help the molecules to pack in a layered structure. Semi-empirical calculations have been performed to predict theoretically the feasibility of intramolecular ground and/or excited state proton transfer reaction/s. Potential energy curves have been generated in the ground (S0) and the lowest excited (S1) singlet states to judge the feasibility of intramolecular single and double proton transfer reactions. Semi-empirical (AM1) calculations suggest that only the excited state intramolecular single proton transfer process is favored both thermodynamically and kinetically. No other prototropic processes are theoretically feasible.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Salicylaldazine; Intramolecular Proton Transfer; Hydrogen Bonding; Potential Energy Curve
ID Code:67438
Deposited On:31 Oct 2011 04:53
Last Modified:31 Oct 2011 04:53

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