In this research, fluorine substituent influence on the electronic structure, 14NQR and electronic spectra of carbo-borazine molecule was explored at M062X/6-311G(d,p) level of theory. Energetic stability of possible isomers was examined. QTAIM results illustrated ring critical points (RCP) and the electrostatic potential of RCP reported. The curvature of electron density perpendicular to ring plane at RCP was considered to exploring of aromaticity of these molecules. The ELF map were used to description of chemical bonds (C-H, C-B, C-N, B-F, N-F and B-N) in the studied molecules. Natural transition orbital (NTO) analysis was employed to origin of corresponding transition of λmax value. Fluorine substituent influence on the computed λmax and 14N NQR parameters values was studied.
ChauvinRCarbomersI. “Carbomers”. I. A general concept of expanded molecules. Tetrahedron Lett1995; 36: 397–400.
2.
ChauvinR. “Carbomers”. II. En route to [C,C]6carbo-benzene. Tetrahedron Lett1995; 36: 401–404.
3.
MaravalVChauvinR. From macrocyclic oligo-acetylenes to aromatic RingCarbo-Mers. Chem Rev2006; 106: 5317–5343.
4.
GodardCLepetitCChauvinR. DFT Exploration of structural and magnetic properties of [n]Annulene ring Carbomers. Chem Commun2000: 1833–1834. doi:10.1039/b005961g.
5.
LepetitCGodardCChauvinR. Aromaticity and Homoaromaticity of Annulene ring Carbomers. New J Chem2001; 25: 572–580.
6.
LepetitCSilviBChauvinR. ELF Analysis of out-of-plane aromaticity and in-plane Homoaromaticity in carbo Annulenes and Pericyclynes. J Phys Chem A2003; 107: 464–473.
7.
ZouCLepetitCCoppelY, et al.Ring carbo-Mers: From questionable Homoaromaticity to bench aromaticity. Pure Appl Chem2006; 78: 791–811.
8.
SonciniAFowlerPWLepetitC, et al.Aromaticity of ring carbo-Mers of [N]Annulenes and [N]cycloalkanes. Phys Chem Chem Phys2008; 10: 957–964.
9.
ChauvinRLepetitCMaravalV, et al.Variation of aromaticity by twisting or expanding the ring content. Pure Appl Chem2010; 82: 769–800.
10.
KuwataniYWatanabeNUedaI. Synthesis of the first 3,6,9,15,18,18-hexa-substituted-1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulenes with D6h-symmetry. Tetrahedron Lett1995; 36: 119–122.
11.
SuzukiRTsukudeHWatanabeN, et al.Synthesis, structure and properties of 3,9,15-tri- and 3,6,9,12,15,18-hexasubstituted dodecadehydro[18]annulenes (C18H3R3 and C18R6) with D6h-symmetry. Tetrahedron1998; 54: 2477–2496.
12.
ZhuCDuhayonCRomero-BorjaD, et al.Hexaaryl-carbo-benzenes revisited: A novel synthetic route, crystallographic data, and prospects of electrochemical behavior. New J Chem2017; 41: 3908–3914.
13.
JalifeSAudiffredMIslasR, et al.The inorganic analogues of carbo-benzene. Chem Phys Lett2014; 610–611: 209–212.
14.
HayPJ. Gaussian Basis sets for molecular calculations. The representation of orbitals in transition-metal atoms. J Chem Phys1977; 66: 4377–4384.
15.
KrishnanRBinkleyJSSeegerR, et al.Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys1980; 72: 650–654.
16.
McLeanADChandlerGS. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms. J Chem Phys1980; 72: 5639–5648.
17.
WachtersAJH. Gaussian Basis set for molecular Wavefunctions containing third-row atoms. J Chem Phys1970; 52: 1033–1036.
18.
ZhaoYTruhlaDG. Comparative DFT study of van der Waals complexes: rare-gas dimers, alkaline-earth dimers, zinc dimer, and zinc-rare-gas dimers. J Phys Chem2006; 110: 5121–5129.
19.
FrischMJTrucksGWSchlegelHB, et al. 2013, Gaussian, Inc., Wallingford CT.
BlancoMPandásAMMckeeWC. Bay-type H···H “bonding” in cis-2-butene and related species: QTAIM versus NBO description. J Comput Chem2014; 35: 1499–1508.
22.
PendasAMBlancoMAFranciscoE. Chemical fragments in real space: Definitions, properties, and energetic decompositions. J Comput Chem2007; 28: 161–184.
23.
BlancoMAPendasAMFranciscoE. Interacting quantum atoms: A correlated energy decomposition scheme based on the quantum theory of atoms in molecules. J Chem Theory Comput2005; 1: 1096–1109.
24.
FranciscoEPendasAMBlancoMAA, et al.Theory. Comput.2006; 2: 90–102.
25.
KeithTA. AIMAll, Version 19.10.12. Overland Park, KS: TK Gristmill Software, 2019.
26.
LuTChenF. Atomic dipole moment corrected Hirshfeld population method. . J Theor Comput Chem2012; 11: 63.
27.
LuTChenF. Meaning and functional form of the electron localization function. Acta Phys -Chim Sin2011; 27: 2786–2792.
28.
HowardSTKrygowskiTM. Benzenoid hydrocarbon aromaticity in terms of charge density descriptors. Can J Chem1997; 75: 1174–1181.
29.
LuTChenF. Quantitative analysis of molecular surface based on improved marching Tetrahedra algorithm. J Mol Graph Model2012; 38: 314–323.
