Synthesis of a Novel Hydrazone of Thieno[2,3-d]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations-Reference-Cited by-同舟云学术

Synthesis of a Novel Hydrazone of Thieno[2,3-d]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations

Published:2023-02-23 Issue:3 Volume:13 Page:384
ISSN:2073-4352
Container-title:Crystals
language:en
Short-container-title:Crystals

Author:

Altowyan Mezna Saleh¹^ORCID,Haukka Matti²^ORCID,Soliman Saied M.³,Barakat Assem⁴^ORCID,Boraei Ahmed T. A.⁵,Sopaih Manar⁵

Affiliation:

1. Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi Arabia

2. Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland

3. Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, Egypt

4. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

5. Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt

Abstract

The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N′-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very good yield from the reaction of the triketoester 1 or ninhydrin 2 with the exocyclic acetohydrazide 3 in methanol. Good-quality crystals of 4 were obtained by recrystallization of the compound from the DMF/MeOH solvent mixture. The target product 4 crystallized in the triclinic crystal system and P-1 space group. The topology analysis of molecular packing indicated that the H…H (30.4%), O…H (22.0%) and H…C (17.0%) contacts are the most dominant intermolecular interactions in the crystal of 4, while the O…H, N…H, H…C, N…C, O…C, C…C and O…O are the only contacts which have shorter interaction distances than the vdWs radii sum of the interacting atoms. The structure of 4 is optimized and the calculated structure showed good agreement with the experimental one. Additionally, MEP, HOMO, LUMO and the reactivity descriptors were calculated.

Funder

Princess Nourah bint Abdulrahman University

Publisher

MDPI AG

Subject

Inorganic Chemistry,Condensed Matter Physics,General Materials Science,General Chemical Engineering

Link

https://www.mdpi.com/2073-4352/13/3/384/pdf

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