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Volume 2009
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Short Note

4-{[(3-Cyanophenyl)imino]methyl}-3-hydroxyphenyl Tetradecanoate

by
Sie-Tiong Ha
1,*,
Siew-Teng Ong
1,
Yee-Ting Chong
2 and
Guan-Yeow Yeap
3
1
Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia
2
Department of Science & Engineering, Centre for Foundation Studies, Universiti Tunku Abdul Rahman, Building PE, No. 1 Jalan 13/4, 46200 Petaling Jaya, Selangor, Malaysia
3
Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800 Minden, Penang, Malaysia
*
Author to whom correspondence should be addressed.
Molbank 2009, 2009(4), M630; https://doi.org/10.3390/M630
Submission received: 26 August 2009 / Accepted: 13 October 2009 / Published: 14 October 2009
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Abstract

:
A new Schiff base ester, 4-{[(3-cyanophenyl)imino]methyl}-3-hydroxyphenyl tetradecanoate, was synthesized and its IR, 1H NMR, 13C NMR and MS spectroscopic data are presented.

Graphical Abstract

Schiff bases have received a considerable amount of attention from many researchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3,4].

Synthesis

4-Formyl-3-hydroxyphenyl tetradecanoate was previously prepared via Steglich esterification [5]. In a round-bottom flask, a mixture of the 4-formyl-3-hydroxyphenyl tetradecanoate (1.74 g, 5.0 mmol), 3-aminobenzonitrile (0.59 g, 5.0 mmol) and absolute ethanol (50 mL) was refluxed with stirring for 3 hours. The reaction mixture was filtered and the solvent was removed from the filtrate by evaporation. Recrystallization from absolute ethanol gave the title compound as a yellow solid (0.96 g, 43%).
Molbank 2009 m630 i001
Melting point: 85.2 °C.
MS (EI): M+ (m/z) = 448 (4).
IR (KBr, cm-1): 3439 (O-H), 2958, 2916, 2849 (C-H aliphatic); 1760 (C=O ester); 1620 (C=N); 1576, 1498 (C=C aromatic).
1H NMR (400 MHz, CDCl3): δ/ppm 0.88 (t, 3H, J = 7.0 Hz, CH3), 1.29-1.45 {m, 20H, CH3(CH2)10-}, 1.73 (q, 2H, J = 7.4 Hz, -CH2CH2COO-), 2.56 (t, 2H, J = 7.5 Hz, -CH2COO-), 6.73 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.79 (d, 1H, J = 2.2 Hz, Ar-H), 7.41 (d, 1H, J = 8.5 Hz, Ar-H), 7.48 (dd, 1H, J = 2.2, 7.6 Hz, Ar-H), 7.52-7.53 (m, 1H, Ar-H), 7.54 (d, 1H, J = 2.2 Hz, Ar-H), 7.56 (dd, 1H, J = 2.2, 8.5 Hz, Ar-H), 8.61 (s, 1H, CH=N), 12.92 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm 172.1 (COO), 164.2 (CH=N), 118.6 (C≡N), 162.9, 155.6, 149.7, 134.1, 130.8, 126.4, 124.9, 117.1, 114.0, 113.8, 111.0, 110.0 (aromatic carbons), 34.84 (‑CH2COO‑), 25.26 (-CH2CH2COO-), 32.32, 30.08, 30.05, 30.00, 29.85, 29.75, 29.65, 29.47, 23.09 (CH3(CH2)14-), 14.52 (CH3).
Elemental analysis: Calculated for C28H36N2O3 C, 74.97%, H, 8.09%, N, 6.24%; Found: C, 75.10%, H, 8.00%, N, 6.19%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The main author (S.T. Ha) would like to thank Universiti Tunku Abdul Rahman for the financial support and research facilities.

References and Notes

  1. Hadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahedron 1987, 43, 1345–1360. [Google Scholar] [CrossRef]
  2. Hadjoudis, E.; Rontoyianni, A.; Ambroziak, K.; Dziembowska, T.; Mavridis, I.M. Photochromism and thermochromism of solid trans-N,N'-bis(salicylidene)-1,2-cyclohexanediamines and trans-N,N'-bis-(2-hydroxynaphylidene)-1,2-cyclohexanediamine. J. Photochem. Photobiol. A: Chem. 2004, 162, 521–530. [Google Scholar] [CrossRef]
  3. Oshima, A.; Momotake, A.; Arai, T. Photochromism, thermochromism, and solvatochromism of naphthalene-based analogues of salicylideneaniline in solution. J. Photochem. Photobiol. A: Chem. 2004, 162, 473–479. [Google Scholar] [CrossRef]
  4. Yeap, G.Y.; Ha, S.T.; Ishizawa, N.; Suda, K.; Boey, P.L.; Mahmood, W.A.K. Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3-methoxybenzalideneanilines. J. Mol. Struct. 2003, 658, 87–99. [Google Scholar] [CrossRef]
  5. Ha, S.T.; Ong, S.T.; Chong, Y.T.; Yeap, G.Y. 4-{[(3-Chlorophenyl)imino]methyl}-3-hydroxyphenyl myristate. Molbank 2009, 2009, M629. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

Ha, S.-T.; Ong, S.-T.; Chong, Y.-T.; Yeap, G.-Y. 4-{[(3-Cyanophenyl)imino]methyl}-3-hydroxyphenyl Tetradecanoate. Molbank 2009, 2009, M630. https://doi.org/10.3390/M630

AMA Style

Ha S-T, Ong S-T, Chong Y-T, Yeap G-Y. 4-{[(3-Cyanophenyl)imino]methyl}-3-hydroxyphenyl Tetradecanoate. Molbank. 2009; 2009(4):M630. https://doi.org/10.3390/M630

Chicago/Turabian Style

Ha, Sie-Tiong, Siew-Teng Ong, Yee-Ting Chong, and Guan-Yeow Yeap. 2009. "4-{[(3-Cyanophenyl)imino]methyl}-3-hydroxyphenyl Tetradecanoate" Molbank 2009, no. 4: M630. https://doi.org/10.3390/M630

APA Style

Ha, S. -T., Ong, S. -T., Chong, Y. -T., & Yeap, G. -Y. (2009). 4-{[(3-Cyanophenyl)imino]methyl}-3-hydroxyphenyl Tetradecanoate. Molbank, 2009(4), M630. https://doi.org/10.3390/M630

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