Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Mar 3;6(10):7047-7057.
doi: 10.1021/acsomega.0c06323. eCollection 2021 Mar 16.

Synthesis of Diaminopyrimidine Sulfonate Derivatives and Exploration of Their Structural and Quantum Chemical Insights via SC-XRD and the DFT Approach

Akbar Ali  1 , Muhammad Khalid  2 , Muhammad Nawaz Tahir  3 , Muhammad Imran  4 , Muhammad Ashfaq  3 , Riaz Hussain  5 , Mohammed A Assiri  4   6 , Imran Khan  3
Affiliations

Synthesis of Diaminopyrimidine Sulfonate Derivatives and Exploration of Their Structural and Quantum Chemical Insights via SC-XRD and the DFT Approach

Akbar Ali et al. ACS Omega. .

Abstract

Two heterocyclic compounds named 2,6-diaminopyrimidin-4-ylnaphthalene-2-sulfonate (A) and 2,6-diaminopyrimidin-4-yl4-methylbenzene sulfonate (B) were synthesized. The structures of heterocyclic molecules were established by the X-ray crystallographic technique, which showed several noncovalent interactions as N···H···N, N···H···O, and C-H···O bonding and parallel offset stacking interaction. Hydrogen-bonding interactions were further explored by the Hirshfeld surface (HS) analysis. Nonlinear optical (NLO) and natural bond orbital (NBO) properties were calculated utilizing the B3LYP/6-311G(d,p) level. Frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) were calculated utilizing the time-dependent density functional theory (TD-DFT) at the same level. The NBO analysis showed that the molecular stabilities of compounds A and B were attributed to their large stabilization energy values. The second hyperpolarizability (γtot) values for A and B were obtained as 3.7 × 104 and 2.7 × 104 au, respectively. The experimental X-ray crystallographic and theoretical structural parameters of A and B were found to be in close correspondence. Both the molecules reveal substantial NLO responses that can be significant for their utilization in advanced applications.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Functionalized pyrimidine compounds with their pharmacological potential.
Figure 2
Figure 2
Synthetic pathway of O-aryalsulfonylation of 2,6-diaminopyrimidin-4-ol.
Figure 3
Figure 3
ORTEP diagrams of A and B drawn at a probability level of 50%. Hydrogen atoms are indicated by small circles of arbitrary radii.
Figure 4
Figure 4
Packing illustration of molecules A and B. The H-atoms not involved in H-bonding are omitted for clarity.
Figure 5
Figure 5
Parallel offset stacking interaction of A and B where the distances are presented in angstrom. The H-atoms are not shown for clarity.
Figure 6
Figure 6
Frontier molecular orbitals of A and B, in electronvolts.
Figure 7
Figure 7
MEPs and the color schemes of A and B.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Nagaraj A.; Reddy C. S. Synthesis and biological study of novel bis-chalcones, bis-thiazines and bis-pyrimidines. J. Iran. Chem. Soc. 2008, 5, 262–267. 10.1007/BF03246116. - DOI
    1. Ajani O. O.; Isaac J. T.; Owoeye T. F.; Akinsiku A. A. Exploration of the chemistry and biological properties of pyrimidine as a privilege pharmacophore in therapeutics. Int. J. Biol. Chem. 2015, 9, 148–177. 10.3923/ijbc.2015.148.177. - DOI
    1. Rao N. V.; Vaisalini N B.; Mounika B.; Harika V. L.; Desu P. K.; Nama S. An overview on synthesis and biological activity of pyrimidines. Int. J. Pharm. Chem. Res. 2013, 2, 14–22.
    1. Kim J. M.; Kim S. H.; Kim J.-N. Synthesis of 2, 4, 5-trisubstituted pyrimidines from Baylis-Hillman adducts and amidines. Bull. Korean Chem. Soc. 2007, 28, 2505–2507. 10.5012/bkcs.2007.28.12.2505. - DOI
    1. Almansa C.; de Arriba A. F.; Cavalcanti F. L.; Gómez L. A.; Miralles A.; Merlos M.; García-Rafanell J.; Forn J. Synthesis and SAR of a new series of COX-2-selective inhibitors: pyrazolo [1, 5-a] pyrimidines. J. Med. Chem. 2001, 44, 350–361. 10.1021/jm0009383. - DOI - PubMed
    2. Gupta J. K.; Chaudhary A.; Dudhe R.; Varuna K.; Sharma P.; Verma P. A review on the synthesis and therapeutic potential of pyrimidine derivatives. Int. J. Pharma. Sci. Res 2010, 1, 34–49.
    3. Asobo P. F.; Wahe H.; Mbafor J. T.; Nkengfack A. E.; Fomum Z. T.; Sopbue E. F.; Dopp D. Heterocycles of biological importance. Part 5. The formation of novel biologically active pyrimido [1, 2-a] benzimidazoles from allenic nitriles and aminobenzimidazoles. J. Chem. Soc., Perkin Trans. 1 2001, 1, 457–461. 10.1039/b005511p. - DOI

LinkOut - more resources