Abstract
Three diaryl oxalate derivatives, bis(4-chlorophenyl)oxalate, bis(2, 6-dichlorophenyl)oxalate and bis(2, 4, 6-trichlorophenyl)oxalate, have been synthesized and characterized via X-ray single crystal diffraction, differential scanning calorimetry, thermogravimetric analysis and infrared spectra, for the purpose of studying the influence of chlorine substitution on the crystal structures of diaryl oxalate. This work has demonstrated that, depending on the position and number, chlorine substitution will influence the molecular geometries and stacking modes of diaryl oxalate by tuning the types and numbers of intermolecular interactions.
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References
E.R.T. Tiekink, K. Vittal (eds.), Organic Crystal Engineering (Wiley, Chichester, 2010)
D. Braga, F. Greponi, Making Crystals by Design: Methods, Techniques and Applications (Wiley-VCH, Chichester, 2007)
G.R. Desiraju (ed.), Crystal Design-Structure and Function, Perspectives in Supramolecular Chemistry (Wiley, Chichester, 2003)
E. Weber (ed.), Design of Organic Solids, Topics in Current Chemistry (Springer, New York, 1998)
A.D. Burrows, Encyclopedia of Supramolecular Chemistry (CRC, Boca Raton, 2004)
D.M.P. Mingos, Supramolecular Assembly Via Hydrogen Bonds I and II, Structure and Bonding (Springer, New York, 2004)
D.N. Chin, J.A. Zerkowski, J.C. MacDonald, G.M. Whitesides, Organnised Molecular Assemblies in the Solid State (Wiley, Chichester, 1999)
S.A. Barnett, A. Johnston, A.J. Florence, S.L. Price, D.A. Tocher, Cryst. Growth Des. 8, 24–36 (2008)
S. Sengupta, A. Goswami, S. Ganguly, S. Bala, M.K. Bhunia, R. Mondal, Cryst. Eng. Commun. 13, 6136–6149 (2011)
M.A. Abdalrahman, F.F. Awwadi, G.B. Jameson, C.P. Landee, C.G. Saunders, M.M. Turnbull, J.L. Wikaira, Cryst. Eng. Commun. 15, 4309–4320 (2013)
F.F. Awwadi, D. Taher, S.F. Haddad, M.M. Turnbull, Cryst. Growth Des. 14, 1961–1971 (2014)
J. Ashmore, R. Bishop, D.C. Craig, M.L. Scudder, Cryst. Eng. Commun. 4, 194–198 (2002)
P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. Int. ED 47, 6114–6127 (2008)
E. Parisini, P. Metrangolo, T. Pilati, G. Resnati, G. Terraneo, Chem. Soc. Rev. 40, 2267–2278 (2011)
M. Baldrighi, D. Bartesaghi, G. Cavallo, M.R. Chierotti, R. Gobetto, P. Metrangolo, T. Pilati, G. Resnati, G. Terraneo, Cryst. Eng. Commun. 16, 5897–5904 (2014)
A. Mukherjee, S. Tothadi, G.R. Desiraju, Acc. Chem. Res. 47, 2514–2524 (2014)
S.Y. Kazemi, S.M. Abedirad, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 118, 782–786 (2014)
E.A. Chandross, Tetrahedron Lett. 12, 761–765 (1963)
T. Wilson, Photochem. Photobiol. 62, 601–606 (1995)
T. Maruyama, S. Narita, J. Motoyoshiya, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 252, 222–231 (2013)
P.M. Lahti, D.A. Modarelli, A. Inceli, Acta Cryst. C 50, 1308–1312 (1994)
X.R. Zeng, Y. Zhang, X.Z. You, Acta Phys. Chem. Sin. 17, 361–363 (2001)
M.M. Rauhut, N.J. Bridgewater, U.S. Patent 1971,3749679
S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Crystal Explorer 2.0 (University of Western Australia, Perth, 2007)
A. Bondi, J. Phys. Chem. 68, 441–451 (1964)
M.J. Frisch et al., Gaussian 03. Revision A.1 (Gaussian, Inc., Pittsburgh, PA, 2003)
J.T. He, B. Xu, F.P. Chen, H.J. Xia, K.P. Li, L. Ye, W.J. Tian, J. Phys. Chem. C 113, 9892–9899 (2009)
F.P.A. Fabbiani, L.T. Byrne, J.J. McKinnon, M.A. Spackman, Cryst. Eng. Commun. 9, 728–752 (2007)
Y.H. Luo, S.W. Ge, W.T. Song, B.W. Sun, N. J. Chem. 38, 723–729 (2014)
Y.H. Luo, B.W. Sun, Cryst. Eng. Commun. 15, 7490–7497 (2013)
Acknowledgments
This work has been supported by the National Natural Science Foundation of China (Project 21371031) and the International S&T Cooperation program of China (2015DFG42240).
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Wu, DE., Luo, YH., Li, TT. et al. Influence of chlorine substitution on the crystal structures of diaryl oxalate. Res Chem Intermed 43, 1591–1607 (2017). https://doi.org/10.1007/s11164-016-2717-2
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DOI: https://doi.org/10.1007/s11164-016-2717-2