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Synthesis and Crystal Structure of 4-(2-Isopropyl-5-methylcyclohexyloxy)phthalonitrile
Corresponding Author(s) : Wu-Lan Zeng
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
A chiral phthalonitrile compound has been prepared by the reaction of chiral menthol (2-isopropyl-5-methylcyclohexanol) and 4-nitrophthalonitrile with potassium carbonate and DMF at 40 ºC. Its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group P 21 21 21 with a = 6.9073(16) Å, b = 8.0803(19) Å, c = 30.558(8) Å, a = 90°, b = 90º, g = 90º, Mr = 282.38, V = 11705.5(7) Å3, Z = 4, Dc = 1.100 g/cm3, F(000) = 608, μ = 0.069 mm-1, R = 0.0690 and wR = 0.1642 for 1535 observed reflections(I > 2s(I)). In the structure, p…p stacking interactions among phthalonitrile rings make the molecule more stable and the cyclohexane ring adopts a chair conformation.
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References
N. Nombona, E. Antunes and T. Nyokong, Dyes Pigm., 86, 68 (2010).
N. Kobayashi, Coord. Chem. Rev., 219, 99 (2001).
K. Suda, S Nakajima, Y. Satoh and T. Takanami, Chem. Commun., 1255 (2009).
E.A. LukCentyanets, J. Porphyrins Phthalocyanines, 3, 424 (1999).
L. Brunsveld, H. Zhang, M. Glasbeek and J.A.J.M. Vekemans, J. Am. Chem. Soc., 122, 6175 (2000).
J.J.M. Halls, C.A. Walsh, N.C. Greenham, E.A. Marseglia and R.H. Friend, Nature, 376, 498 (1995).
J.M. Rivera, T. Martin and J. Rebek Jr., Science, 279, 1021 (1998).
M. Kimura, H. Ueki and K. Ohta, Langmuir, 22, 5051 (2006).
K. Adachi, K. Chayama and H. Watarai, Langmuir, 22, 1630 (2006).
K. Adachi, K. Chayama and H. Watarai, Chirality, 18, 599 (2006).
G.M. Sheldrick, Acta Cryst., A64, 112 (2008).
Siemens,Area Detector Control and Integration Software, USA (1996).
L. Yu, X. Zhou, Y. Yin, R. Li and T. Peng, Acta Cryst, E66, o2527 (2010).
D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354 (1975).