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New Journal of Chemistry
Page 4 of 5
DOI: 10.1039/C6NJ02622B
COMMUNICATION
New Journal of Chemistry
5
(a) M. D. Esrafili, N. Mohammadirad and M. Solimannejad,
Chemical Physics Letter, 2015, 628, 16-20. (b) S. P. Thomas,
D. Jayatilaka and T. N. G. Row, Phys.Chem.Chem.Phys., 2015,
17, 25411-25420. (c) R. Shukla and D. Chopra, Phys. Chem.
Chem. Phys, 2016, DOI: 10.1039/C6CP05899J.
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Model. 2007, 13, 291-296.
P. Politzer, P. Lane, M. C. Concha, Y. G. Ma and J. S. Murray,
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provided effective support to the interaction; second-order
perturbation theory analysis of the Fock Matrix on the NBO
basis has confirmed that the conformation lock is in nature
intramolecular charge transfer from the C=N lone pair into the
σ*(C—X) antibonding orbital. We believe that the present work
may be the first study on conformation effect of C=N…C−X σ-
Hole interaction.
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7
8
9
P. Politzer, J. S. Murray and M. C. Concha, J. Mol. Model.,
2007, 13, 643.
Experimental
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and S. Kitamura, Carbohydr. Polym., 2014, 99, 432-437. (b) I.
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(c) J. Pitawala, J. Scheers, P. Jacobsson and A. Matic, J. Phys.
Chem. B 2013, 117, 8172-8179.
Synthesis of 1 and 9.
To a solution of ethyl cyanoacetate (0.2 mol) in anhydrous
ethanol (50mL), were added hydrazine (80%, 0.25 mol), the
reaction mixture was stirred at room temperature. The
precipitate was filtered off, washed with anhydrous ethanol and
dried to give pure cyanoacetohydrazide (12 g). As intermediate,
cyanoacetohydrazide (0.1 mol) was dissolved in anhydrous
ethanol (50 mL), and then 4-hydroxy or 2-hydroxybenzaldehyde
(0.1 mol) was added. The reaction mixture was refluxed for 20
min, and then cooled to room temperature. The solid was
collected by filtration, washed with ethanol, and dried to yield
the compound 1 or 9 (15 g) as a crystalline solid. Crystals 1 and
9 suitable for an X-ray analysis were obtained by slow cooling of
a hot acetonitrile solution of the corresponding product.
10 (a) H. Satoh and S. Manabe, Chem. Soc. Rev. 2013, 42, 4297-
4309. (b) A. E. Christina, J. A. Muns, J. Q. A. Olivier, L. Visser,
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11 M. D. Esrafili, N. Mohammadirad and M. Solimannejad,
Chemical Physics Letters, 2015, 628, 16–20.
12 D. Mani and E. Arunan, Phys. Chem. Chem. Phys., 2013, 15,
14377-14383.
13 S. Yourdkhani, T. Korona N. L. Hadipour, Journal of
Computational Chemistry, 2015, 36, 2412-2428.
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Crystal data of compounds 1 and 9
1: C10H9N3O2, M = 203.20, Monoclinic, P21/n, a = 4.7366(4), b =
11.1769(10), c = 18.9660(18) Å , α = 90, β = 97.015(2), γ = 90°, V
= 996.55(15) Å3, Z = 4, T = 296(2) K, Dc = 1.354 g.cm-3; 5454
reflections collected, 1767 unique (Rint = 0.026), 1289 observed
with I > 2σ(I); final R = 0.0345, wR2 = 0.0866, goodness-of-fit S
= 1.01.
9: C10H9N3O2, M = 203.20, Monoclinic, P21/n, a = 4.5944(3), b =
9.3525(4), c = 22.972(3) Å , α = 90, β = 94.883(2), γ = 90°, V =
983.50(15) Å3, Z = 4, T = 296(2) K, Dc = 1.372 g.cm-3; 14740
reflections collected, 2971 unique (Rint = 0.035), 1796 observed
with I > 2σ(I); final R = 0.0496, wR2 = 0.1400, goodness-of-fit S
= 1.01.
18 E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter
and F. Weinhold, NBO Version 3.1, Theoretical Chemistry
Institute, University of Wisconsin, Madison, USA, 1995.
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Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H.
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2009.
ACKNOWLEDGMENTS
We gratefully acknowledge the support from The High
Performance Computing Center of Henan Normal University.
Notes and references
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