Document Type : Short communication

Author

Department of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran

Abstract

In this research study, two Schiff base compounds AP-DHPDB (1) synthesized from the reaction of 2-aminophenol (AP) with 3, 3ʹ-dihydroxy-4, 4ʹ-(propane-1, 2-dieloxy)-dibenzaldehyde (DHPDB) and FA-DHEDB (2) synthesized from the reaction of furfuryl amine (FA) with 3, 3ʹ-dihydroxy-4, 4ʹ-(ethane-1, 2-dieloxy)-dibenzaldehyde (DHEDB) by reflux in methanol as solvent for 2 h. Suitable crystals of 1 and 2 get by slow evaporation of solvent after few days and characterized by elemental analysis. Crystal structures of the title compounds 1 and 2 were determined using the single crystal X-ray diffraction analysis. The title compounds 1 and 2 were found to be in monoclinic and orthorhombic with the space group of C2/c and Pnca, respectively. The unit cell parameter of 1 were a=29/8994(10), b=4.86618(7), c=21.7214(4) Å, b=124.4901(17)° and V=2604.85(12) Å3, and the unit cell parameter of 2 were a=22/3513(7), b=26.0250(7), c=4.6681(9) Å and V=2715(12) Å3. The C-N bond distances around the iminic nitrogen of compound 1 are 1.418 and 1.268 Å, and in compound 2 are 1.467 and 1.269 Å, indicated the single and double bonds, respectively. Also, the bond angles around the iminic nitrogen are distorted from 120° corresponding to sp2 hybrid (N1-C7-C8 = 122.5° and C6-N1-C7 = 119.3° for 1 and N7-C8-C9 = 123.9° and C6-N7-C8 = 116.12° for 2).

Graphical Abstract

Preparation and crystal structures of new schiff bases derived from 3, 3ʹ-dihydroxy-4, 4ʹ-(propane-1, 2-dieloxy)-dibenzaldehyde

Keywords

[1]. Khalaji A.D., Peyghoun S.J., Akbari A., Feizi N., Dusek M., Eigner V. Polyhedron., 2016, 119: 429
[2]. Khalaji A.D., Peyghoun S.J., Akbari A., Feizi N., Dusek M., Eigner V. J. Mol. Struct., 2017, 1127: 511
[3]. Khalaji A.D., Peyghoun S.J., Dusek M., Eigner V. Asian J. Nanosci. Mater., 2019, 2: 201
[4]. Xiang H., Jiang L., Li H.-Y., Zheng X.-D., Li Y. Chin. Chem. Lett., 2013, 24: 49
[5]. Sheikhshoaie I., Davary S., Ramezanpour S. Chem. Method., 2018, 2: 47
[6]. Lee S.K., Tan K.W., Ng S.W., Ooi K.K., Ang K.P., Abdah M.A. Spectrochim. Acta. A., 2014, 121: 101
[7]. Khalaji A.D. Chem. Method., 2019, 3: 635
[8]. Sheikhshoaie I., Tohidiyan Z. Chem. Method., 2019, 3: 30
[9]. Khalaji A.D., Grivani G., Rezaei M., Fejfarova K., Dusek M. Polyhedron., 2011, 30: 2790
[10]. Khalaji A.D., Ghorbani M., Peyghoun S.J., Feizi N., Akbari A., Hornfeck W., Dusek M., Eigner V. Chem. Method., 2019, 3: 707
[11]. Ma X., Cheng J., Liu J., Zhou, X., Xiang H. New. J. Chem., 2015, 39: 492
[12]. Kose M., Ceyhan G., Tumer M., Demirtas I., Gonul I., McKee V. Spectrochim. Acta. A., 2015, 137: 477
[13]. Dalapati S., Alam M.A., Jana S., Guchhait N. J. Fluor. Chem., 2011, 132: 536
[14]. Bayol E., Gurten T., Gurten A.A., Erbil M. Mater. Chem. Phys., 2008, 112: 624
[15]. Leela S., Ramamurthi K., Bhagavannarayana G. Spectrochim. Acta. A., 2009, 74: 78
[16]. Sun Y.-X., You Z.-L., Zhu H.-L. Acta Crystallogr., 2004, E60: o1707
[17]. Naderi E., Jafari A.H., Ehteshamzadeh M., Hosseini M.G. Mater. Chem. Phys., 2009, 115: 852
[18]. Chiririwa H., Aoyi O. Iran. J. Sci. Technol. Trans. Sci., 2017, 41: 1003
[19]. Benarous N., Cherouana A., Aubert E., Durand P., Dahaoui S. J. Mol. Struct., 2016, 1105: 186
[20]. Tanak H., Agar A., Yavuz M. J. Mol. Model., 2010, 16: 577
[21]. Sun Y., Wang Y., Liu Z., Huang C., Yu C. Spectrochim. Acta. A., 2012, 96: 42
[22]. Reimann M.J., Salmon D.R., Horton J.T., Gier E.C., Jefferies L.R. ACS Omega., 2019, 4: 2874
[23]. Berrones-Reyes J., Munoz-Flores B.M., Gomez-Trevino A., Treto-Suarez M.A., Paez-Hernandez D., Schott E., Zarate X., Jimenez-Perez V.M. Mater. Chem. Phys., 2019, 233: 89
[24]. Zhu X., Duan Y., Li P., Fan H., Han T., Huang X. Anal. Method., 2019, 11: 642
[25]. Kumar V., Kumar P., Kumar S., Singhal D., Gupta R. Inorg. Chem., 2019, 58: 10364
[26]. Kjalaji A.D., Fejfarova K., Dusek M. J. Struct. Chem., 2015, 56: 1405
[27]. Kjalaji A.D., Forocgnia A., Fejfarova K., Dusek M. J. Struct. Chem., 2013, 54: 774
[28]. Kjalaji A.D., Ghoran S.H., Rohlicek J., Dusek M. J. Struct. Chem., 2015, 56: 259
[29]. Kjalaji A.D., Ghoran S.H., Pojarova M., Dusek M. J. Struct. Chem., 2015, 56: 1410
[30]. Han J.R., Zhen X.L. Acta. Crystallogr., 2005, E-61: o4073
[31]. Palatinus L., Chapuis G. J. Appl. Crystallogr., 2007, 40: 786
[32]. Petricek V., Dusek M., Palatinus L. Z. Kristallogr., 2014, 229: 345
[33]. Diamonde Crystal and Molecular Structure Visualization Software. http://www.crystalimpact.com