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Vibrational spectra of fluorene, 1-methylfluorene and 1,8-dimethylfluorene

Chakraborty, Shubhadip and Das, Prasanta and Manogaran, Sadasivam and Das, Puspendu K (2013) Vibrational spectra of fluorene, 1-methylfluorene and 1,8-dimethylfluorene. In: VIBRATIONAL SPECTROSCOPY, 68 . pp. 162-169.

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Official URL: http://dx.doi.org/10.1016/j.vibspec.2013.07.001

Abstract

In this paper, we report the gas phase infrared spectra of fluorene and its methylated derivatives using a heated multipass cell and argon as a carrier gas. The observed spectra in the 4000-400 cm(-1) range have been fitted using the modified scaled quantum mechanical force field (SQMFF) calculation with the 6-311G** basis. The advantage of using the modified SQMFF method is that it scales the force constants to find the best fit to the observed spectral lines by minimizing the fitting error. In this way we are able to assign all the observed fundamental bands in the spectra. With consecutive methyl substitutions two sets of bands are found to shift in a systematic way. The set of four aromatic C-H stretching vibrations around 3000 cm(-1) shifts toward lower frequencies while the single most intense aromatic C-H out-of-plane bending mode around 750 cm(-1) shifts toward higher frequencies. The reason for shifting of aromatic C-H stretching frequency toward lower wave numbers with gradual methyl substitution has been attributed to the lengthening of the C-H bonds due to the +I effect of the methyl groups to the ring current as revealed from the calculations. While the unexpected shifting of the aromatic C-H out-of-plane bend toward higher wave numbers with increasing methyl substitution is ascribed to the lowering of the number of adjacent aromatic C-H bonds on the plane of the benzene ring with gradual methyl substitutions. (C) 2013 Elsevier B.V. All rights reserved.

Item Type: Journal Article
Additional Information: copyright for this article belongs to ELSEVIER SCIENCE BV, NETHERLANDS
Keywords: Fluorene; Scaled quantum mechanical force field; Aromatic C-H out-of-plane bend; Inductive effect
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 28 Dec 2013 06:16
Last Modified: 28 Dec 2013 06:16
URI: http://eprints.iisc.ac.in/id/eprint/47987

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