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Three forms of squaric acid with pyrazine and pyridine derivatives: an experimental and theoretical study

Content Provider	Springer Nature Link
Author	Korkmaz, Ufuk Uçar, İbrahim Bulut, Ahmet Büyükgüngör, Orhan
Copyright Year	2011
Abstract	Three new squarate salts were synthesized and combined with experimental and theoretical study on molecular, vibrational, and electronical properties. Squaric acid was crystallized as HSQ$^{−}$ [SQ: squarate] monoanion in [(C$_{13}$H$_{12}$NO$_{2}$)(HC$_{4}$O$_{4}$)] (I), as uncharged H$_{2}$SQ in [(C$_{5}$H$_{5}$N$_{3}$O)(H$_{2}$C$_{4}$O$_{4}$)] (II), and as SQ$^{2−}$ dianion form in [C$_{6}$H$_{9}$N$_{2}$)$_{2}$(C$_{4}$O$_{4}$)] (III). They crystallize in the triclinic and monoclinic crystal system with space group P−1, P2$_{1}$/c, and P2$_{1}$/c, respectively. Crystal structure analysis reveals that, far from forming discrete ionic species in (I) and (II), it is likely that there is large degree of proton sharing between the two hydrogen squarate anions in (I) and between the neutral moieties in (II), with the H atom lying almost symmetrically between the donor and acceptor sites, as evidenced by the long O–H and N–H bonds and short H···O distances. Ab initio calculations have been carried out for three compounds by using DFT/B3LYP and HF methods at 6-31++G(d,p) basis set. Although the supramolecular interactions have some influences on the molecular geometry in solid state phase, calculated data show that the predicted geometries can reproduce the structural parameters. The results of the optimized molecular structure for three compounds obtained on the basis of two models are presented and compared with the experimental X-ray data. Calculated vibrational frequencies are consistent with each other and experimental IR data. The theoretical electronic absorption spectra have been calculated by both TD–DFT and HF–CIS methods. Molecular orbital coefficients analysis suggest that the electronic transitions are mainly assigned to n → π* and π → π* electronic transitions.
Starting Page	1249
Ending Page	1259
Page Count	11
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	22
Issue Number	6
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2011-06-17
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Squaric acid X-ray diffraction Strong hydrogen bonding Vibrational spectra UV–vis Quantum chemical calculations Theoretical and Computational Chemistry Physical Chemistry Computer Applications in Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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