Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid

Azeema Munir; Sidra Ayaz; Afzal Shah; Tayyaba Kokab; Faiza Jan Iftikhar; Anwar-ul-Haq Ali Shah; Muhammad Abid Zia

doi:doi:10.11648/j.ajpc.20211003.12

| Peer-Reviewed

Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid

Azeema Munir, Sidra Ayaz, Afzal Shah, Tayyaba Kokab, Faiza Jan Iftikhar, Anwar-ul-Haq Ali Shah, Muhammad Abid Zia

Published in American Journal of Physical Chemistry (Volume 10, Issue 3)

Received: 21 June 2021 Accepted: 12 July 2021 Published: 24 July 2021

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

Substituents play a major role in influencing the reactivity and biological activity of aromatic compounds. Substituents affect the conductivity of molecular electronic and photoresponsive switches, light harvesting dye-sensitized solar cells and organic electroluminescent devices. A number of quantum mechanical methods corresponding to stabilization energy, charge of substituent active region, energy dispersive analysis, and molecular electrostatic potential help in the description of substituent effect in aromatic systems. In the present work we carried out computational studies for the estimation of chemical and structural properties of a chemical library of nine ortho substituted naphthoic acids. The chemical reactivity of the selected substituted naphthoic acids was assessed from a number of physicochemical properties such as total energy, HOMO-LUMO gap, chemical hardness, binding energy, ionization potential, electron affinity, electronegativity, electrochemical potential, global softness, electrophilicity and dipole moment. The effect of the electron-donor groups on conjugation of ortho substituted naphthoic acid was investigated by correlating the calculated rotational barriers of transition state of cis and trans ortho-substituted naphthoic acids to observe change in single bond length, double bond length, bond angle, dihedral angle, and rotational frequency of carboxylic group of substituted napthoic acids. The rotational barrier correlated with the geometric, atomic, molecular, and spectroscopic parameters. Moreover, quantitative structure–activity relationship (QSAR) analyses was performed and the obtained structural properties were linked with biological activities.

Published in	American Journal of Physical Chemistry (Volume 10, Issue 3)
DOI	10.11648/j.ajpc.20211003.12
Page(s)	45-53
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2021. Published by Science Publishing Group

Keywords

Ortho-substituted Naphthoic Acids, Rotational Barrier, Substituent Effect, Quantitative Structure–Activity Relationship

References

[1]	Kiselev, E., Barrett, M. O., Katritch, V., Paoletta, S., Weitzer, C. D., Brown, K. A., Hammes, E., Yin, A. L., Zhao, Q., Stevens, R. C. (2014) Exploring a 2-naphthoic acid template for the structure-based design of P2Y14 receptor antagonist molecular probes. ACS chemical biology, 9 (12), 2833-2842. https://pubs.acs.org/doi/abs/10.1021/cb500614p.
[2]	Varenikov, A., Shapiro, E., Gandelman, M. (2021) Decarboxylative Halogenation of Organic Compounds. Chemical Reviews, 121, 412–484. https://doi.org/10.1021/acs.chemrev.0c00813.
[3]	Chen, H., Ouyang, L., Liu, J., Shi, W.-J., Chen, G., Zheng, L. (2019) Synthesis of multisubstituted 1-naphthoic acids via Ru-catalyzed C–H activation and double-alkyne annulation under air. The Journal of Organic Chemistry, 84 (20), 12755-12763. https://doi.org/10.1021/acs.joc.9b00926.
[4]	Gao, B., Chen, L., Chen, T. (2015) Effect of electron-donating substituent groups on aromatic ring on photoluminescence properties of complexes of benzoic acid-functionalized polysulfone with Eu (III) ions. Physical Chemistry Chemical Physics, 17 (38), 25322-25332. https://doi.org/10.1039/C5CP03300D.
[5]	Fujita, T., Koshimizu, K., Kawazu, K., Imai, S., Mitsui, T. (1960) The plant growth activity of 1-naphthoic acid derivatives and their related compounds (Commemoration Issue Dedicated to Professor Sankichi Takei on the Occasion of His Retirement). Bulletin of the Institute for Chemical Research, Kyoto University, 38 (1), 76-93. https://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/75752/1/chd038_1_076.pdf.
[6]	Bell, S. G., Zhou, R., Yang, W., Tan, A. B., Gentleman, A. S., Wong, L. L., Zhou, W. (2012), Investigation of the substrate range of CYP199A4: Modification of the partition between hydroxylation and desaturation activities by substrate and protein engineering. Chemistry–A European Journal, 18 (52), 16677-16688. https://doi.org/10.1002/chem.201202776.
[7]	Soriano-Correa, C., Barrientos-Salcedo, C., Francisco-Márquez, M., Sainz-Díaz, C. I. (2018), Computational study of substituent effects on the acidity, toxicity and chemical reactivity of bacteriostatic sulfonamides. Journal of Molecular Graphics and Modelling, 81, 116-124. https://doi.org/10.1016/j.jmgm.2018.02.006.
[8]	Zhan, X., Barlow, S., Marder, S. R. (2009) Substituent effects on the electronic structure of siloles. Chemical communications 2009 (15), 1948-1955. https://doi.org/10.1039/B822760H.
[9]	Frisch, M., Trucks, G., Schlegel, H., Scuseria, G., Robb, M., Cheeseman, J., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. Wallingford CT 2009.
[10]	Zhang, M., Wang, X., Yang, T., Qiao, Y., Wei, D. (2021) Theoretical model for N-heterocyclic carbene-catalyzed decarboxylation reactions. Organic Chemistry Frontiers. https://doi.org/10.1039/D1QO00413A.
[11]	Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Physical review A, 38 (6), 3098. https://doi.org/10.1103/PhysRevA.38.3098
[12]	Manzhos, S. (2020) Machine learning for the solution of the Schrödinger equation. Machine Learning: Science and Technology, 1 (1), 013002. https://iopscience.iop.org/article/10.1088/2632-2153/ab7d30/meta.
[13]	Senet, P. (1997) Chemical hardnesses of atoms and molecules from frontier orbitals. Chemical physics letters, 275 (5-6), 527-532. https://doi.org/10.1016/S0009-2614(97)00799-9.
[14]	Ali, A., Khalid, M., Rehman, M. A., Anwar, F., Zain-Ul-Aabidin, H., Akhtar, M. N., Khan, M. U., Braga, A. A. C., Assiri, M. A., Imran, M. (2020) An Experimental and Computational Exploration on the Electronic, Spectroscopic, and Reactivity Properties of Novel Halo-Functionalized Hydrazones. ACS omega, 5 (30), 18907-18918. https://doi.org/10.1021/acsomega.0c02128.
[15]	Foresman, J., Frisch, E. Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian, 269 p, Gaussian Inc., Pittsburgh, Pennsylvania, (1996).
[16]	Firsch, M., Trucks, G., Schlegel, H., Scuseria, G., Robb, M., Cheeseman, J., Montgomery Jr, J., Vreven, T., Kudin, K., Burant, J. Gaussian-03, Revision E. 01, Gaussian, Inc., Wallingford CT, (2004).
[17]	Chattaraj, P. K., Maiti, B. (2003) HSAB principle applied to the time evolution of chemical reactions. Journal of the American Chemical Society, 125 (9), 2705-2710. https://doi.org/10.1021/ja0276063.
[18]	Parr, R. G., Pearson, R. G. (1983) Absolute hardness: companion parameter to absolute electronegativity. Journal of the American chemical society, 105 (26), 7512-7516. https://doi.org/10.1021/ja00364a005.
[19]	Pearson, R.; Sen, K.; Mingos, D. Springer, Chemical hardness: structure and bonding, Springer, Berlin, (1993).
[20]	Parr, R. G., Szentpály, L. v., Liu, S. (1999) Electrophilicity index. Journal of the American Chemical Society, 121 (9), 1922-1924. https://doi.org/10.1021/ja983494x.
[21]	Govindarajan, M., Karabacak, M. (2012) FT-IR, FT-Raman and UV spectral investigation; computed frequency estimation analysis and electronic structure calculations on 1-nitronaphthalene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 85 (1), 251-260. https://doi.org/10.1016/j.saa.2011.10.002.
[22]	Liu, S. (2005) Dynamic behavior of chemical reactivity indices in density functional theory: A Bohn-Oppenheimer quantum molecular dynamics study. Journal of Chemical Sciences, 117 (5), 477-483. https://doi.org/10.1007/BF02708352.
[23]	Koopmans, T. (1934) Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica, 1 (1), 104-113. https://doi.org/10.1016/S0031-8914(34)90011-2.
[24]	Duda-Seiman, C., Duda-Seimana, D., Putz, M., Ciubotariub, D. (2007) QSAR modelling of anti-HIV activity with HEPT derivatives. Digest Journal of Nanomaterials and Biostructures, 2 (2), 207-219.
[25]	Ishikawa, T., Hirano, H., Saito, H., Sano, K., Ikegami, Y., Yamaotsu, N., Hirono, S. (2012) Quantitative structure-activity relationship (QSAR) analysis to predict drug-drug interactions of ABC transporter ABCG2. Mini reviews in medicinal chemistry, 12 (6), 505-514. https://doi.org/10.2174/138955712800493825.
[26]	Prades, J., Cirera, A., Morante, J. (2009) Ab initio calculations of NO2 and SO2 chemisorption onto non-polar ZnO surfaces. Sensors and Actuators B: Chemical, 142 (1), 179-184. https://doi.org/10.1016/j.snb.2009.08.017.
[27]	Joseph, R., Ramanujam, B., Acharya, A., Rao, C. P. (2009) Lower rim 1, 3-di {bis (2-picolyl)} amide derivative of calix (4) arene (L) as ratiometric primary sensor toward Ag+ and the complex of Ag+ as secondary Sensor toward Cys: experimental, computational, and microscopy studies and INHIBIT logic gate properties of L. The Journal of organic chemistry, 74 (21), 8181-8190. https://doi.org/10.1021/jo901676s.
[28]	Malik, A., Singh, H., Andrabi, M., Husain, S. A., Ahmad, S. (2006) Databases and QSAR for cancer research. Cancer informatics, 2, 117693510600200002. https://doi.org/10.1177/117693510600200002.
[29]	Munir, A., Shah, A., Piro, B. (2018) Development of a selective electrochemical sensing platform for the simultaneous detection of Tl+, Cu2+, Hg2+, and Zn2+ ions. Journal of The Electrochemical Society, 165 (10), B399. https://doi.org/10.1149/2.0441810jes/meta.
[30]	de Paiva, R. K., Silva, J. F. d., Moreira, H. A., Pinto, O. G., Camargo, L. T., Naves, P. L., Camargo, A. J., Ribeiro, L., Ramos, L. M. (2019) Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2, 4-dione Derivatives. Journal of the Brazilian Chemical Society, 30 (1), 164-172. http://dx.doi.org/10.21577/0103-5053.20180167.
[31]	Holder, A. J., Ye, L., Eick, J. D., Chappelow, C. C. (2006) An Application of QM‐QSAR to Predict and Rationalize the Refractive Index of a Wide Variety of Simple Organic/Organosilicon Molecules. QSAR & Combinatorial Science, 25 (4), 342-349. https://doi.org/10.1002/qsar.200510178.
[32]	Almi, Z., Belaidi, S., Lanez, T., Tchouar, N. (2014) Structure Activity Relationships, QSAR Modeling and Drug-like calculations of TP inhibition of 1, 3, 4-oxadiazoline-2-thione Derivatives. International Letters of Chemistry, Physics and Astronomy, 18, 113--124. https://www.infona.pl/resource/bwmeta1.element.baztech-4fe5cba9-cd91-499c-b298-085ab415b464/tab/summary.
[33]	Joseph, O. A., Babatomiwa, K., Niyi, A., Olaposi, O., Olumide, I. (2019) Molecular docking and 3D qsar studies of C000000956 as a potent inhibitor of bace-1. Drug research, 69 (08), 451-457. http://dx.doi.org/10.1055/a-0849-9377.
[34]	Guo, S., Tao, X., Duan, Y., Cui, X., Zhang, W., Li, H., Ying, X. (2020) A new naphthoic acid from Portulaca oleracea L. and its Activities. Latin American Journal of Pharmacy, 39 (8), 1575-1578.
[35]	Kasai, H., Kawasaki, Y., Kawai, K. (2021) 1, 4-Dihydroxy-2-naphthoic Acid Sulfate: A Promising Constipation Preventive Agent. Journal of Food and Nutrition Research, 9 (2), 96-101. http://dx.doi.org/10.12691/jfnr-9-2-6.
[36]	Mhaidat, I., Taha, Z., Al Momani, W., Hijazi, A. (2019) Photoconductivity, Antioxidant, and Antimicrobial Activities of Some Acenaphthenequinone Derivatives. Russian Journal of General Chemistry, 89 (12), 2584-2590. https://doi.org/10.1134/S1070363219120399.
[37]	Nam, K. Y., Damodar, K., Lee, Y., Park, L. S., Gim, J. G., Park, J. P., Jeon, S. H., Lee, J. T. (2021), Design and Synthesis of π-Extended Resveratrol Analogues and In Vitro Antioxidant and Anti-Inflammatory Activity Evaluation. Molecules, 26 (3), 646. https://doi.org/10.3390/molecules26030646.
[38]	Evans, W., Fernley, H., Griffiths, E. (1965) Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads. The ring-fission mechanism. Biochemical Journal, 95 (3), 819. https://doi.org/10.1042/bj0950819.
[39]	Rogoff, M. H., Wender, I. (1957) 3-Hydroxy-2-naphthoic acid as an intermediate in bacterial dissimilation of anthracene. Journal of bacteriology, 74 (1), 108. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC289892/.
[40]	Marr, E. K., Stone, R. W. (1961) Bacterial oxidation of benzene. Journal of bacteriology, 81 (3), 425. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC279025/.
[41]	Rogoff, M. H. (1962) Chemistry of oxidation of polycyclic aromatic hydrocarbons by soil pseudomonads. Journal of bacteriology, 83 (5), 998-1004. https://jb.asm.org/content/83/5/998/article-info.

Cite This Article

Plain Text BibTeX RIS

APA Style

Azeema Munir, Sidra Ayaz, Afzal Shah, Tayyaba Kokab, Faiza Jan Iftikhar, et al. (2021). Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid. American Journal of Physical Chemistry, 10(3), 45-53. https://doi.org/10.11648/j.ajpc.20211003.12

Copy | Download

ACS Style

Azeema Munir; Sidra Ayaz; Afzal Shah; Tayyaba Kokab; Faiza Jan Iftikhar, et al. Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid. Am. J. Phys. Chem. 2021, 10(3), 45-53. doi: 10.11648/j.ajpc.20211003.12

Copy | Download

AMA Style

Azeema Munir, Sidra Ayaz, Afzal Shah, Tayyaba Kokab, Faiza Jan Iftikhar, et al. Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid. Am J Phys Chem. 2021;10(3):45-53. doi: 10.11648/j.ajpc.20211003.12

Copy | Download

@article{10.11648/j.ajpc.20211003.12,
  author = {Azeema Munir and Sidra Ayaz and Afzal Shah and Tayyaba Kokab and Faiza Jan Iftikhar and Anwar-ul-Haq Ali Shah and Muhammad Abid Zia},
  title = {Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid},
  journal = {American Journal of Physical Chemistry},
  volume = {10},
  number = {3},
  pages = {45-53},
  doi = {10.11648/j.ajpc.20211003.12},
  url = {https://doi.org/10.11648/j.ajpc.20211003.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajpc.20211003.12},
  abstract = {Substituents play a major role in influencing the reactivity and biological activity of aromatic compounds. Substituents affect the conductivity of molecular electronic and photoresponsive switches, light harvesting dye-sensitized solar cells and organic electroluminescent devices. A number of quantum mechanical methods corresponding to stabilization energy, charge of substituent active region, energy dispersive analysis, and molecular electrostatic potential help in the description of substituent effect in aromatic systems. In the present work we carried out computational studies for the estimation of chemical and structural properties of a chemical library of nine ortho substituted naphthoic acids. The chemical reactivity of the selected substituted naphthoic acids was assessed from a number of physicochemical properties such as total energy, HOMO-LUMO gap, chemical hardness, binding energy, ionization potential, electron affinity, electronegativity, electrochemical potential, global softness, electrophilicity and dipole moment. The effect of the electron-donor groups on conjugation of ortho substituted naphthoic acid was investigated by correlating the calculated rotational barriers of transition state of cis and trans ortho-substituted naphthoic acids to observe change in single bond length, double bond length, bond angle, dihedral angle, and rotational frequency of carboxylic group of substituted napthoic acids. The rotational barrier correlated with the geometric, atomic, molecular, and spectroscopic parameters. Moreover, quantitative structure–activity relationship (QSAR) analyses was performed and the obtained structural properties were linked with biological activities.},
 year = {2021}
}

Copy | Download

TY  - JOUR
T1  - Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid
AU  - Azeema Munir
AU  - Sidra Ayaz
AU  - Afzal Shah
AU  - Tayyaba Kokab
AU  - Faiza Jan Iftikhar
AU  - Anwar-ul-Haq Ali Shah
AU  - Muhammad Abid Zia
Y1  - 2021/07/24
PY  - 2021
N1  - https://doi.org/10.11648/j.ajpc.20211003.12
DO  - 10.11648/j.ajpc.20211003.12
T2  - American Journal of Physical Chemistry
JF  - American Journal of Physical Chemistry
JO  - American Journal of Physical Chemistry
SP  - 45
EP  - 53
PB  - Science Publishing Group
SN  - 2327-2449
UR  - https://doi.org/10.11648/j.ajpc.20211003.12
AB  - Substituents play a major role in influencing the reactivity and biological activity of aromatic compounds. Substituents affect the conductivity of molecular electronic and photoresponsive switches, light harvesting dye-sensitized solar cells and organic electroluminescent devices. A number of quantum mechanical methods corresponding to stabilization energy, charge of substituent active region, energy dispersive analysis, and molecular electrostatic potential help in the description of substituent effect in aromatic systems. In the present work we carried out computational studies for the estimation of chemical and structural properties of a chemical library of nine ortho substituted naphthoic acids. The chemical reactivity of the selected substituted naphthoic acids was assessed from a number of physicochemical properties such as total energy, HOMO-LUMO gap, chemical hardness, binding energy, ionization potential, electron affinity, electronegativity, electrochemical potential, global softness, electrophilicity and dipole moment. The effect of the electron-donor groups on conjugation of ortho substituted naphthoic acid was investigated by correlating the calculated rotational barriers of transition state of cis and trans ortho-substituted naphthoic acids to observe change in single bond length, double bond length, bond angle, dihedral angle, and rotational frequency of carboxylic group of substituted napthoic acids. The rotational barrier correlated with the geometric, atomic, molecular, and spectroscopic parameters. Moreover, quantitative structure–activity relationship (QSAR) analyses was performed and the obtained structural properties were linked with biological activities.
VL  - 10
IS  - 3
ER  -

Copy | Download

Author Information

Azeema Munir

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
Sidra Ayaz

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
Afzal Shah

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
Tayyaba Kokab

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
Faiza Jan Iftikhar

Department of Chemistry, National University of Technology, Islamabad, Pakistan
Anwar-ul-Haq Ali Shah

Institute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan
Muhammad Abid Zia

Department of Chemistry, University of Education Attock, Attock, Pakistan

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Azeema Munir, Sidra Ayaz, Afzal Shah, Tayyaba Kokab, Faiza Jan Iftikhar, et al. (2021). Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid. American Journal of Physical Chemistry, 10(3), 45-53. https://doi.org/10.11648/j.ajpc.20211003.12

Copy | Download

ACS Style

Azeema Munir; Sidra Ayaz; Afzal Shah; Tayyaba Kokab; Faiza Jan Iftikhar, et al. Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid. Am. J. Phys. Chem. 2021, 10(3), 45-53. doi: 10.11648/j.ajpc.20211003.12

Copy | Download

AMA Style

Azeema Munir, Sidra Ayaz, Afzal Shah, Tayyaba Kokab, Faiza Jan Iftikhar, et al. Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid. Am J Phys Chem. 2021;10(3):45-53. doi: 10.11648/j.ajpc.20211003.12

Copy | Download

@article{10.11648/j.ajpc.20211003.12,
  author = {Azeema Munir and Sidra Ayaz and Afzal Shah and Tayyaba Kokab and Faiza Jan Iftikhar and Anwar-ul-Haq Ali Shah and Muhammad Abid Zia},
  title = {Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid},
  journal = {American Journal of Physical Chemistry},
  volume = {10},
  number = {3},
  pages = {45-53},
  doi = {10.11648/j.ajpc.20211003.12},
  url = {https://doi.org/10.11648/j.ajpc.20211003.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajpc.20211003.12},
  abstract = {Substituents play a major role in influencing the reactivity and biological activity of aromatic compounds. Substituents affect the conductivity of molecular electronic and photoresponsive switches, light harvesting dye-sensitized solar cells and organic electroluminescent devices. A number of quantum mechanical methods corresponding to stabilization energy, charge of substituent active region, energy dispersive analysis, and molecular electrostatic potential help in the description of substituent effect in aromatic systems. In the present work we carried out computational studies for the estimation of chemical and structural properties of a chemical library of nine ortho substituted naphthoic acids. The chemical reactivity of the selected substituted naphthoic acids was assessed from a number of physicochemical properties such as total energy, HOMO-LUMO gap, chemical hardness, binding energy, ionization potential, electron affinity, electronegativity, electrochemical potential, global softness, electrophilicity and dipole moment. The effect of the electron-donor groups on conjugation of ortho substituted naphthoic acid was investigated by correlating the calculated rotational barriers of transition state of cis and trans ortho-substituted naphthoic acids to observe change in single bond length, double bond length, bond angle, dihedral angle, and rotational frequency of carboxylic group of substituted napthoic acids. The rotational barrier correlated with the geometric, atomic, molecular, and spectroscopic parameters. Moreover, quantitative structure–activity relationship (QSAR) analyses was performed and the obtained structural properties were linked with biological activities.},
 year = {2021}
}

Copy | Download

TY  - JOUR
T1  - Computational Studies of the Role of Substituents on the Reactivity and Biological Activities of Naphthoic Acid
AU  - Azeema Munir
AU  - Sidra Ayaz
AU  - Afzal Shah
AU  - Tayyaba Kokab
AU  - Faiza Jan Iftikhar
AU  - Anwar-ul-Haq Ali Shah
AU  - Muhammad Abid Zia
Y1  - 2021/07/24
PY  - 2021
N1  - https://doi.org/10.11648/j.ajpc.20211003.12
DO  - 10.11648/j.ajpc.20211003.12
T2  - American Journal of Physical Chemistry
JF  - American Journal of Physical Chemistry
JO  - American Journal of Physical Chemistry
SP  - 45
EP  - 53
PB  - Science Publishing Group
SN  - 2327-2449
UR  - https://doi.org/10.11648/j.ajpc.20211003.12
AB  - Substituents play a major role in influencing the reactivity and biological activity of aromatic compounds. Substituents affect the conductivity of molecular electronic and photoresponsive switches, light harvesting dye-sensitized solar cells and organic electroluminescent devices. A number of quantum mechanical methods corresponding to stabilization energy, charge of substituent active region, energy dispersive analysis, and molecular electrostatic potential help in the description of substituent effect in aromatic systems. In the present work we carried out computational studies for the estimation of chemical and structural properties of a chemical library of nine ortho substituted naphthoic acids. The chemical reactivity of the selected substituted naphthoic acids was assessed from a number of physicochemical properties such as total energy, HOMO-LUMO gap, chemical hardness, binding energy, ionization potential, electron affinity, electronegativity, electrochemical potential, global softness, electrophilicity and dipole moment. The effect of the electron-donor groups on conjugation of ortho substituted naphthoic acid was investigated by correlating the calculated rotational barriers of transition state of cis and trans ortho-substituted naphthoic acids to observe change in single bond length, double bond length, bond angle, dihedral angle, and rotational frequency of carboxylic group of substituted napthoic acids. The rotational barrier correlated with the geometric, atomic, molecular, and spectroscopic parameters. Moreover, quantitative structure–activity relationship (QSAR) analyses was performed and the obtained structural properties were linked with biological activities.
VL  - 10
IS  - 3
ER  -

Copy | Download