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Pdf 528.87 K Iranian Journal of Organic Chemistry Vol. 9, No. 1 (2017) 1981-1993 M. Nabati et al. Theoretical studies on the structural properties, aromaticity and reactivity of 1H-phosphole derivatives Mehdi Nabatia,*, Mehdi Hasanvand Mofradb, Maliheh-alsadat Kermanianc, Saman Sarshard aChemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz, Iran bFaculty of Liberal arts, Shahid Beheshti University, Tehran, Iran cEnglish language Department, Faculty of Foreign Languages, Pishva Branch, Islamic Azad University, Varamin, Iran dPhysics Department, Faculty of Science, Lorestan University, Khorramabad, Iran Received: November 2016; Revised: December 2016; Accepted: January 2017 Abstract: In the present research work, we have done a comparative study of 1H-phosphole molecule and its derivatives substituted on C2 or C3 atoms with B3LYP/6-311++G(d,p) level of theory. Here, we have done an investigation of their structures, aromaticity, and global and local reactivity of 1H-phosphole molecule and its derivatives. The aromaticity property of all compounds was considered by NICS and BIRD indices. Also, we have used frontier orbital HOMO-LUMO energies and relative calculations (global hardness, electronic chemical potential, electronegativity, global softness, nucleophilicity index and electrophilicity index) to explain the stability and reactive nature of 1H-phosphole and its derivatives. The reactivity of different atoms in each molecule was studied by Fukui functions. Keywords: DFT study, 1H-phosphole, Aromaticity, Global reactivity, Local reactivity. Introduction The 1H-phosphole ring is an organic molecule with the chemical formula C4H4PH. This heterocyclic Laszlo Nyulaszi investigated on the substituents compound is the phosphorus analog of the pyrrole effect on the aromatization of phosphole ring in 1995 molecule. Recently, the organic materials based on the [5]. Klaus Eichele and his co-workers studied the phosphole ring received much attention due to their phosphorus chemical shift tensors of phosphole characteristic optical and electronic properties [1].The derivatives by 31P NMR spectroscopy technique of phosphole compound has a low-lying lowest powder samples [6].In 2001, Eric Mattmann unoccupied molecular orbital (LUMO) and low et.al.prepared the trivalent 7-phosphanobornenes by aromaticity [2]. Pentaphenylphosphole is the first enhancing the dienic reactivity of the phosphole phosphole compound that was prepared in 1953 [3]. materials [7].The de-aromatizing of the phosphole Hughes and Srivanavit worked on thermal and compounds were investigated by Mattmann group. photochemical ring expansion of some phosphole They used the quantum-chemical density functional derivatives. In another work, churchman et.al studied theory (DFT) computations for study of this property the site of protonation in phosphole derivatives. They [8]. Jeanne Crassous and Regis Reau synthesized the found the 1H-phospholium salts stabilized by complex π-conjugated phosphole derivatives in 2008. They also transition metal ions [4]. studied the optoelectronic functions and coordination chemistry of those compounds [9].Some of the phospholeP-oxide molecules were reported by Arihiro *Corresponding author. Tel: +98 (413) 4327501, Fax: +98 Saito et.al. in 2009 [10]. The palladium-catalyzed (413) 4327501, E-mail: [email protected] 1981 Iranian Journal of Organic Chemistry Vol. 9, No. 1 (2017) 1981-1993 M. Nabati et al. direct synthesis of phosphole derivatives was first phosphole derivatives containing different substituents reported by the Katsuaki Baba group in 2013 [11]. on positions 2 or 3. Recently, the various materials based on this Results and discussion heterocyclic compound were synthesized and studied theoretically [12]. In the present research work, the The structure of the positions 2 and 3 substituted 1H- main aim of my investigations is the study of structural phospholes is shown in Scheme 1. properties, aromaticities and reactivities of various 1H- Scheme 1: The studied 1H-phosphole derivatives substituted at positions 2 and 3. electron-donating substituents is in range 1.70-1.73 and The present study is divided into three parts. The 1.81-1.82 Aº, respectively. Exceptionally, this bond in first part studies the structural properties of the studied 2-(difluoromethyl)-1H-phosphole and is 1.815 Aº. molecules. In second part, aromaticity and stability of Also, the P-C5 bond of 1H-phosphole-2-sulfonic acid the compounds are investigated. Finally, the third part polarized by –SO3H group and is 1.817 Aº. The data of this research work is related to the study of the of the Table 1 shows the range of C2-C3, C3-C4 and global and local reactivity of all molecules. C4-C5 bonds lengths of all compounds are 1.35-1.41, 1.40-1.46, 1.35-1.41 and 1.07-1.08 Aº, respectively. Bond lengths, bond angles and dihedral angles of The P-H6 bond of molecules containing electron- the 1H-phosphole derivatives donating substituents is longer than the electron- The bond lengths data of the 1H-phosphole withdrawing groups. derivatives substituted on C2 are collected in Table 1. Table 2 indicates the bond lengths data of the 1H- It can be seen from the data, the geometry of the phosphole compounds substituted on position 3. molecules changes depending on the substituent. The The electronegative substituents cause the shorter P-C2 P-C2 bond length of 1H-phosphole ring containing and P-C5 bonds lengths than the electron-donation electron withdrawing substituents on position 2 varies substituents. These bonds distances are in range 1.71- between 1.72 and 1.74 Aº. Also, the electron donating 1.73 and 1.81-1.82 Aº for molecules containing groups cause longer distances. We can see the P-C2 electronegative and electron-donating substituents, distance of phosphole compound containing methyl respectively.The C-C bonds distances vary from 1.35 and t-butyl substituents is 1.737 and 1.842 Aº, to 1.45 Aº. The short P-H6 bonds are related to the 1H- respectively. Hence, the more electron-donating phospholes with electron-withdrawing substituents on substituent cause the longer distance of P-C2 bond. position 3. The distance of C-H bonds of all molecules The distance of this bond for the molecules containing is about 1.08 Aº. –CH2F, -CHF2 and –CF3 substituents are 1.736, 1.828 It can be seen from the data, the angles order is: C-C- and 1.731 Aº, respectively. Exceptionally, the P-C2 C > C-C-P > C-P-C. The C-C-C angles vary from 113 bond distance of 1H-phosphole substituted by –CHF2 degree to 117 degree. The range of C-C-P angles of group is longer than the –CH2F and –CF3 groups. molecules is 105-111 degree. The small and big C-C-P Probably, the asymmetric steric bulk distribution of the angles relate to the 1H-phosphole compounds F atoms of this substituent to hydrogen atom causes the containing electron-withdrawing and electron-donating longer distance of P-C2 bond. Also, the –SO3H substituents, respectively. Also, the C-P-C bond angles substituent polarizes the P-C2 bond. For this reason, are in range 88-99 degree. The molecules with the distance of this bond in the molecule containing – electron-withdrawing substituents on position 2 have SO3H substituent is 1.824 Aº. The P-C5 bond distance bigger C-P-C bond angles than the electron-donating of the molecules with electron-withdrawing and substituents. 1982 Iranian Journal of Organic Chemistry Vol. 9, No. 1 (2017) 1981-1993 M. Nabati et al. Table 1: The bond lengths data of the 1H-phosphole derivatives substituted on C2 atom. Y P-C2 C2-C3 C3-C4 C4-C5 C5-P P-H6 C2-Y C3-H8 C4-H9 C5-H10 H 1.725 1.390 1.420 1.390 1.725 1.391 1.078 1.082 1.082 1.078 CH3 1.737 1.390 1.422 1.386 1.730 1.392 1.501 1.084 1.083 1.078 CH2F 1.736 1.388 1.422 1.385 1.729 1.392 1.498 1.081 1.082 1.078 CHF2 1.828 1.355 1.453 1.354 1.815 1.421 1.483 1.086 1.084 1.082 CF3 1.731 1.392 1.415 1.391 1.720 1.391 1.483 1.081 1.082 1.078 tBu 1.842 1.357 1.457 1.352 1.814 1.422 1.522 1.084 1.085 1.082 F 1.739 1.375 1.425 1.385 1.733 1.390 1.344 1.081 1.082 1.077 Cl 1.733 1.384 1.421 1.388 1.727 1.391 1.736 1.082 1.082 1.078 Br 1.730 1.385 1.421 1.388 1.727 1.391 1.892 1.082 1.082 1.078 CN 1.736 1.402 1.410 1.394 1.717 1.391 1.409 1.081 1.082 1.078 COOH 1.733 1.400 1.409 1.398 1.715 1.390 1.456 1.081 1.082 1.078 CONH2 1.731 1.399 1.412 1.396 1.717 1.390 1.474 1.083 1.082 1.078 OH 1.834 1.354 1.456 1.353 1.820 1.423 1.358 1.085 1.085 1.081 OCH3 1.842 1.358 1.457 1.352 1.820 1.423 1.349 1.082 1.085 1.081 SH 1.834 1.356 1.456 1.353 1.820 1.421 1.771 1.084 1.085 1.082 SCH3 1.839 1.358 1.455 1.353 1.819 1.421 1.768 1.084 1.085 1.082 SO3H 1.824 1.356 1.451 1.354 1.817 1.421 1.759 1.084 1.084 1.082 NO2 1.732 1.392 1.408 1.400 1.715 1.390 1.429 1.081 1.082 1.078 NO 1.743 1.406 1.400 1.407 1.708 1.392 1.397 1.081 1.082 1.078 NH2 1.847 1.361 1.452 1.353 1.819 1.423 1.385 1.085 1.086 1.081 N(CH3)2 1.855 1.370 1.449 1.354 1.814 1.425 1.378 1.082 1.086 1.081 Table 2: The bond lengths data of the 1H-phosphole derivatives substituted on C3 atom.
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