NDLI: Infrared spectra of diphenylphthalide and polydiphenylenephthalide

Content Provider	Springer Nature Link
Author	Shishlov, N. M. Khursan, S. L.
Copyright Year	2011
Abstract	The splitting of the ν(C=O) absorption band (AB) of about 12 cm$^{−1}$ is found in the IR spectra of diphenylphthalide (DPP) in the crystalline phase and CCl$_{4}$ solution. In the crystalline phase, this splitting is likely to be caused by the inequivalence of DPP molecules in the crystallographic cell, while in the solution, by the dimerization of DPP molecules via dipole-dipole and/or hydrogen bonds. A theoretical low-frequency shift of the ν(C=O) AB for a complex of two DPP molecules (in comparison with a single molecule) is 14 cm$^{−1}$ in the PBE/3ξ approximation, which is close to the experimentally observed splitting. In two quantum chemical approximations (B3LYP/6-311G(d,p) (I) and PBE/3ξ (II)) the optimal structure and vibrational spectrum of DPP are calculated. Approximation I better reproduces the intensities, whereas approximation II better reproduces the IR frequencies of the DPP spectrum. Almost all 48 ABs of the IR spectrum of DPP are assigned to theoretical normal vibrations (modes). Based on the potential energy distribution over natural coordinates and the visualization of vibrations, experimental ABs (and the corresponding modes) are assigned to the stretching and bending vibrations of certain bonds in the DPP molecule. In particular, ABs at 1107 cm$^{−1}$ and 970 cm$^{−1}$ are assigned to the ν(-OC-O-) and ν(-C-O-) stretching vibrations, respectively, of the DPP lactonic ring, which differs from the previously accepted assignment. The results of the interpretation of the DPP spectrum are used to assign a number of ABs in the IR spectrum of polydiphenylenephthalide (PDP), for which DPP is a model compound. According to the calculations in approximation II of the vibrational spectrum of a model valence-bonded dimeric molecule, the intense complex AB at 800–870 cm$^{−1}$ in the IR spectrum of PDP is mainly due to the out-of-plane bending vibrations of C-H bonds in the 1,4-substituted benzene rings of polymer biphenyl moieties and the bending vibrations of the lactonic ring.
Starting Page	272
Ending Page	286
Page Count	15
File Format	PDF
ISSN	00224766
Journal	Journal of Structural Chemistry
Volume Number	52
Issue Number	2
e-ISSN	15738779
Language	English
Publisher	SP MAIK Nauka/Interperiodica
Publisher Date	2011-05-27
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	vibrational spectra density functional theory phthalides polyarylenephthalides phenolphthalein Physical Chemistry Inorganic Chemistry Solid State Physics Atomic/Molecular Structure and Spectra Atomic, Molecular, Optical and Plasma Physics
Content Type	Text
Resource Type	Article
Subject	Materials Chemistry Physical and Theoretical Chemistry Inorganic Chemistry

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