Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

被引:14
作者
Cakmak, Sukriye [1 ]
Kansiz, Sevgi [4 ]
Azam, Mohammad [5 ]
Veyisoglu, Aysel [1 ]
Yakan, Hasan [2 ]
Min, Kim [3 ]
机构
[1] Sinop Univ, Vocat Sch Hlth Serv, Dept Med Serv & Tech, TR-57000 Sinop, Turkey
[2] Ondokuz Mayis Univ, Dept Sci & Math Educ, TR-55139 Samsun, Turkey
[3] Dongguk Univ, Dept Safety Engn, Gyeongju 780714, Gyeongbuk, South Korea
[4] Samsun Univ, Dept Fundamental Sci, Fac Engn, TR-55420 Samsun, Turkey
[5] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
来源
ACS OMEGA | 2022年 / 7卷 / 20期
关键词
CARBOXYLIC-ACID ANHYDRIDES; INTERMOLECULAR INTERACTIONS; ALDEHYDES; VISUALIZATION; ESTERS; CDC; DFT;
D O I
10.1021/acsomega.2c00879
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a novel anhydride derivative, 3-acetoxy-2-methylbenzoic anhydride (AMA), obtained from the interaction of 3-acetoxy-2-methylbenzoyl chloride with 3-acetoxy-2-methylbenzoic acid. The synthesized compound was characterized by elemental analysis, IR, H-1 NMR, and C-13 NMR spectroscopic studies and single-crystal X-ray crystallography which revealed the crystallization of AMA as monoclinic with space group P2(1)/c. A Hirshfeld surface analysis was performed to record various intermolecular interactions, indicating the stabilization of the AMA structure by the intermolecular weak C-H center dot center dot center dot O hydrogen bonds and pi center dot center dot center dot pi interactions. The title compound was screened for antibacterial and antifungal activities using a serial dilution technique under aseptic conditions. The results indicate that the title compound has significant antibacterial properties but showed no antifungal behavior.
引用
收藏
页码:17192 / 17201
页数:10
相关论文
共 49 条
[1]   Regioselective transition metal-free acylation of coumarins via cross-dehydrogenative coupling reaction of coumarins and aldehydes [J].
Adib, Mehdi ;
Rajai-Daryasarei, Saideh ;
Pashazadeh, Rahim ;
Tajik, Mahnaz ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2016, 57 (33) :3701-3705
[2]   Highly functionalized N-1-(2-pyridinylmethyl)-3,5-bis[(E)- arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis, characterization, crystal structure and DFT studies [J].
Al-thamili, Dhaifallah M. ;
Almansour, Abdulrahman, I ;
Arumugam, Natarajan ;
Kansiz, Sevgi ;
Dege, Necmi ;
Soliman, Saied M. ;
Azam, Mohammad ;
Kumar, Raju Suresh .
JOURNAL OF MOLECULAR STRUCTURE, 2020, 1222
[3]  
[Anonymous], 2013, APEX2
[4]   Single-Crystal Investigation, Hirshfeld Surface Analysis, and DFT Study of Third-Order NLO Properties of Unsymmetrical Acyl Thiourea Derivatives [J].
Ashfaq, Muhammad ;
Tahir, Muhammad Nawaz ;
Muhammad, Shabbir ;
Munawar, Khurram Shahzad ;
Ali, Akbar ;
Bogdanov, Georgii ;
Alarfaji, Saleh S. .
ACS OMEGA, 2021, 6 (46) :31211-31225
[5]   Chemistry of naphthalene diimides [J].
Bhosale, Sheshanath V. ;
Jani, Chintan H. ;
Langford, Steven J. .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :331-342
[6]   Spectroscopic Insight into Tetrahedrally Distorted Square Planar Copper(II) Complex: XRD/HSA, Physicochemical, DFT, and Thermal Investigations [J].
Boshaala, Ahmed ;
Abrahem, Abrahem F. ;
Almughery, Abdulla Ali ;
Al-Zaqri, Nabil ;
Zarrouk, Abdelkader ;
Lgaz, Hassane ;
Warad, Ismail .
CRYSTALS, 2021, 11 (10)
[7]   Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity [J].
Cakmak, Sukriye ;
Kirca, Basak Kosar ;
Veyisoglu, Aysel ;
Yakan, Hasan ;
Ersanli, Cem Cuneyt ;
Kutuk, Halil .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2022, 78 :201-+
[8]   Natural products with maleic anhydride structure: Nonadrides, tautomycin, chaetomellic anhydride, and other compounds [J].
Chen, Xiaolong ;
Zheng, Yuguo ;
Shen, Yinchu .
CHEMICAL REVIEWS, 2007, 107 (05) :1777-1830
[9]   A NEW ANTIBIOTIC, TAUTOMYCIN [J].
CHENG, XC ;
KIHARA, T ;
KUSAKABE, H ;
MAGAE, J ;
KOBAYASHI, Y ;
FANG, RP ;
NI, ZF ;
SHEN, YC ;
KO, K ;
YAMAGUCHI, I ;
ISONO, K .
JOURNAL OF ANTIBIOTICS, 1987, 40 (06) :907-909
[10]   A one-step procedure for the monoacylation of symmetrical 1,2-diols [J].
Clarke, PA ;
Kayaleh, NE ;
Smith, MA ;
Baker, JR ;
Bird, SJ ;
Chan, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5226-5231