NOVEL PHOTOSYNTHESIS OF 5,8A-DICHLORO-2-(4- METHOXYPHENYL)-8AH-CHROMENE FROM ITS CHALCONE ISOMER AND FT-IR, 1 H AND 13 C NMR SPECTROSCOPIC INVESTIGATION
Keywords:
Chalcone, Chromene, FT-IR, NMR, LC/Q-TOF/MS, CHNO.
Abstract
In the presence of alcoholic alkali, the base-catalyzed aldol condensation of equimolar quantities of
substituted acetophenones and aldehydes to give good yields of condensation product. This reaction is
known as the Claisen-Schmidt condensation. The Trans-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)prop-
2-en-1-one (trans 2,6-methoxy chalcone) was synthesised by Clasien Schmidt reaction, then it exposed to
the Xenon lamp to prepare the 5,8a-dichloro-2-(4-methoxyphenyl)-8aH-chromene (2,6-methoxy
chromene). A number of techniques were used to characterise the mentioned two products such as, thin
layer chromatography, FT-IR, 1H and 13C nuclear magnetic resonance, liquid
chromatography/quadrupole time-of-flight mass spectrometry and elemental analysis (CHNO).
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References
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Journal of Molecular Structure, 1176, 838–
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Substituted Flavylium Salts. European
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EJOC2699%3E3.0.CO;2-I
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Sarojini, B. K. (2015). Molecular structure,
FT-IR, NBO, HOMO and LUMO, MEP and
first order hyperpolarizability of (2E)-1-(2,4-
Dichlorophenyl)-3-(3,4,5-trimethoxyphenyl)
prop-2-en-1-one by HF and density functional
methods. Spectrochimica Acta - Part A:
Molecular and Biomolecular Spectroscopy,
135, 81–91.
https://doi.org/10.1016/j.saa.2014.06.140
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(2015). Spectrometric Identification of
Organic Compounds Eighth Edition. John
Wiley & Sons, Inc.
https://doi.org/10.1017/CBO9781107415324.0 04
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systematic approach,CRC Press, Washington,
DC.
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JOHN WILEY & SONS, LTD.
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Mani, P. and Jayaprakash, A. (2008).
Molecular structure and vibrational spectra of
3-chloro-4-fluoro benzonitrile by ab initio HF
and density functional method.
Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy, 71, 1134–1139.
Wen, R., Lv, H. N., Jiang, Y., & Tu, P. F. (2018).
Anti-inflammatory flavone and chalcone
derivatives from the roots of Pongamia pinnata
(L.) Pierre. Phytochemistry, 149, 56–63.
https://doi.org/10.1016/j.phytochem.2018.02.0
05
Xue, Y., An, L., Zheng, Y., Zhang, L., Gong, X.,
Qian, Y., & Liu, Y. (2012 b). Structure and
electronic spectral property of coumarin-
chalcone hybrids: A comparative study using
conventional and long-range corrected hybrid
functionals. Computational and Theoretical
Chemistry, 981, 90–99.
https://doi.org/10.1016/j.comptc.2011.11.050
Xue, Y., Liu, Y., An, L., Zhang, L., Yuan, Y., Mou,
J., … Zheng, Y. (2011). Electronic structures
and spectra of quinoline chalcones: DFT and
TDDFT-PCM investigation. Computational
and Theoretical Chemistry, 965(1), 146–153.
https://doi.org/10.1016/j.comptc.2011.01.042
Xue, Y., Zheng, Y., An, L., Zhang, L., Qian, Y., Yu,
D., … Liu, Y. (2012 a). A theoretical study of
the structure-radical scavenging activity of
hydroxychalcones. Computational and
Theoretical Chemistry, 982, 74–83.
https://doi.org/10.1016/j.comptc.2011.12.020
Zhou, D., Xie, D., He, F., Song, B., & Hu, D. (2018).
Antiviral properties and interaction of novel
chalcone derivatives containing a purine and
benzenesulfonamide moiety. Bioorganic and
Medicinal Chemistry Letters, 28(11), 2091–
2097.
https://doi.org/10.1016/j.bmcl.2018.04.042
Balali, E. (2019). Prediction of chalcone
derivative cytotoxicity activity against MCF-7
human breast cancer cell by Monte Carlo
method. Journal of Molecular Structure, 1181,
305–311.
https://doi.org/10.1016/j.molstruc.2018.12.089
Bruice, P. Y. (2016). Organic chemistry Eighth
Edition. Pearson Education, Inc. Pearson
Education.
Chen, X., Liu, Z., Meng, R., Shi, C., & Guo, N.
(2017). Antioxidative and anticancer
properties of Licochalcone A from licorice.
Journal of Ethnopharmacology, 198, 331–337.
https://doi.org/10.1016/j.jep.2017.01.028
Chidan Kumar, C. S., Govindarasu, K., Fun, H. K.,
Kavitha, E., Chandraju, S., & Quah, C. K.
(2015). Synthesis, molecular structure,
spectroscopic characterization and quantum
chemical calculation studies of (2E)-1-(5-
chlorothiophen-2-yl)-3-(2,3,4-
trimethoxyphenyl)prop-2-en-1-one. Journal of
Molecular Structure, 1085, 63–77.
https://doi.org/10.1016/j.molstruc.2014.12.052
Colthup, N. B., Daly, L. H., & Wiberley, S. E.
(1990). Introduction to Infrared and Raman
Spectroscopy,Academic Press, New York.
Elzupir, A. O., Ali, M. K. M., Hussein, R. A. H.,
Ibrahem, M. A., Al-muhanna, M. K., &
Ibnaouf, K. H. (2018). Molecular structure ,
frontier molecular orbital and spectral analysis
of dimethylamino chalcones efficient lasing
dyes. Journal of Molecular Structure. https://doi.org/10.1016/j.molstruc.2018.10.035
Espinoza-Hicks, J.C., Nápoles-Duarte, J.M., Nevárez-
Moorillón, G.V., Camacho-Dávila, A. and
Rodríguez-Valdez, L. M. (2016). Synthesis,
electronic, and spectral properties of novel
geranylated chalcone derivatives: a theoretical
and experimental study. Journal of Molecular
Modeling, 22, 253.
https://doi.org/10.1007/s00894-016-3114-x
Gussoni, M., Castiglioni, C., Ramos, M.N., Rui, M.
and Zerbi, G. (1990). Infrared intensities: from
intensity parameters to an overall
understanding of the spectrum. Journal of
Molecular Structure, 224, 445–470.
Joseph, L., Sajan, D., Shettigar, V., Chaitanya, K.,
Misra, N., & Sundius, T. (2013). Synthesis ,
crystal growth , thermal studies and scaled
quantum chemical studies of structural and
vibrational spectra of the highly ef fi cient
organic NLO crystal :, 141, 248–262.
https://doi.org/10.1016/j.matchemphys.2013.0
5.007
Kucerova-Chlupacova, M., Dosedel, M., Kunes, J.,
Soltesova-Prnova, M., Majekova, M., &
Stefek, M. (2018). Chalcones and their
pyrazine analogs: synthesis, inhibition of
aldose reductase, antioxidant activity, and
molecular docking study. Monatshefte Fur
Chemie, 149(5), 921–929.
https://doi.org/10.1007/s00706-018-2146-6
Kumar, A., Deval, V., Tandon, P., Gupta, A., &
Deepak, E. D. (2014). Experimental and
theoretical (FT-IR, FT-Raman, UV–vis,
NMR) spectroscopic analysis and first order
hyperpolarizability studies phenyl]-1-(4-
nitrophenyl)-prop-2-en-1-one using density
functional theory. Spectrochim. Acta, A, 130,
41–53.
https://doi.org/10.1016/j.saa.2014.03.072
Mooney, E. F. (1964). The infra-red spectra of
chloro-and bromobenzene derivatives—II.
Nitrobenzenes. Spectrochimica Acta,
20(1955).
Opletalová, V., Hartl, J., Palát, K., & Patel, A.
(2000). Conformational analysis of 2-hydroxy-
2’,5’-diazachalcones. Journal of
Pharmaceutical and Biomedical Analysis,
23(1), 55–59. https://doi.org/10.1016/S0731-
7085(00)00263-6
Pavia, D.L., Lampman, G.M., Kriz, G.S. and Vyvyan,
J. A. (2014). Introduction to Spectroscopy
Fifth Edition. Cengage Learning; 2014.
https://doi.org/10.1119/1.1935107
Puzzarini C, Penocchio E, Biczysko M, B. V. (2014).
Molecular Structure and Spectroscopic
Signatures of Acrolein:Theory Meets
Experiment. The Journal of Physical
Chemistry A, 188(33), 6648–6656.
Renuka, V., Revathi, B. K., Jonathan, D. R., Priya,
M. K., & Asirvatham, P. S. (2019). Synthesis,
growth and characterization of a new NLO
active chalcone derivative - 4-chloro-N-{3-
[(2E)-3-(methoxyphenyl)prop-2-
Enoyl]phenyl}benzamide monohydrate.
Journal of Molecular Structure, 1176, 838–
846.
https://doi.org/10.1016/j.molstruc.2018.09.021
Roque, A., Lodeiro, C., Pina, F., Maestri, M.,
Ballardini, R., & Balzani, V. (2002).
Photochromic Properties of 3-Methyl-
Substituted Flavylium Salts. European
Journal of Organic Chemistry, 2002(16),
2699. Retrieved from
http://doi.wiley.com/10.1002/1099-
0690(200208)2002:16%3C2699::AID-
EJOC2699%3E3.0.CO;2-I
Sheena Mary, Y., Yohannan Panicker, C., Anto, P.
L., Sapnakumari, M., Narayana, B., &
Sarojini, B. K. (2015). Molecular structure,
FT-IR, NBO, HOMO and LUMO, MEP and
first order hyperpolarizability of (2E)-1-(2,4-
Dichlorophenyl)-3-(3,4,5-trimethoxyphenyl)
prop-2-en-1-one by HF and density functional
methods. Spectrochimica Acta - Part A:
Molecular and Biomolecular Spectroscopy,
135, 81–91.
https://doi.org/10.1016/j.saa.2014.06.140
Silverstein RM, Webster FX, Kiemle DJBruno, L.
(2015). Spectrometric Identification of
Organic Compounds Eighth Edition. John
Wiley & Sons, Inc.
https://doi.org/10.1017/CBO9781107415324.0 04
Smith, B. (1999). Infrared spectral interpretation: a
systematic approach,CRC Press, Washington,
DC.
Socrates, G. (2001). Infrared and Raman
Characteristic Group Frequencies Contents
Third Edition JOHN WILEY & SONS, LTD.
JOHN WILEY & SONS, LTD.
Sundaraganesan, N., Meganathan, C., Joshua, B.D.,
Mani, P. and Jayaprakash, A. (2008).
Molecular structure and vibrational spectra of
3-chloro-4-fluoro benzonitrile by ab initio HF
and density functional method.
Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy, 71, 1134–1139.
Wen, R., Lv, H. N., Jiang, Y., & Tu, P. F. (2018).
Anti-inflammatory flavone and chalcone
derivatives from the roots of Pongamia pinnata
(L.) Pierre. Phytochemistry, 149, 56–63.
https://doi.org/10.1016/j.phytochem.2018.02.0
05
Xue, Y., An, L., Zheng, Y., Zhang, L., Gong, X.,
Qian, Y., & Liu, Y. (2012 b). Structure and
electronic spectral property of coumarin-
chalcone hybrids: A comparative study using
conventional and long-range corrected hybrid
functionals. Computational and Theoretical
Chemistry, 981, 90–99.
https://doi.org/10.1016/j.comptc.2011.11.050
Xue, Y., Liu, Y., An, L., Zhang, L., Yuan, Y., Mou,
J., … Zheng, Y. (2011). Electronic structures
and spectra of quinoline chalcones: DFT and
TDDFT-PCM investigation. Computational
and Theoretical Chemistry, 965(1), 146–153.
https://doi.org/10.1016/j.comptc.2011.01.042
Xue, Y., Zheng, Y., An, L., Zhang, L., Qian, Y., Yu,
D., … Liu, Y. (2012 a). A theoretical study of
the structure-radical scavenging activity of
hydroxychalcones. Computational and
Theoretical Chemistry, 982, 74–83.
https://doi.org/10.1016/j.comptc.2011.12.020
Zhou, D., Xie, D., He, F., Song, B., & Hu, D. (2018).
Antiviral properties and interaction of novel
chalcone derivatives containing a purine and
benzenesulfonamide moiety. Bioorganic and
Medicinal Chemistry Letters, 28(11), 2091–
2097.
https://doi.org/10.1016/j.bmcl.2018.04.042
Published
2020-12-11
How to Cite
YOUSIF, A. A., & FADHIL, G. F. (2020). NOVEL PHOTOSYNTHESIS OF 5,8A-DICHLORO-2-(4- METHOXYPHENYL)-8AH-CHROMENE FROM ITS CHALCONE ISOMER AND FT-IR, 1 H AND 13 C NMR SPECTROSCOPIC INVESTIGATION. Journal of Duhok University, 23(2), 118-134. https://doi.org/10.26682/sjuod.2020.23.2.14
Section
Pure and Engineering Sciences
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