Synthesis Crystal Structures Density Functional

Authors: Philip Z Mannes Manpreet Kaur Evans O Onyango Gordon W Gribble Jerry P Jasinski

Publish Date: 2017/02/09

Volume: 47, Issue: 1-2, Pages: 10-21

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Abstract

Three new derivatives of 1phenylsulfonylindole 3nitro1phenylsulfonyl1Hindol2amine I C14H11N3O4S Ntertbutyl3nitro1phenylsulfonyl1Hindol2amine II C18H19N3O4S and tertbutyl 4phenylsulfonyl1 Pelkey Gribble Tetrahedron Lett 385603–5606 1997 3triazolo45bindole14Hcarboxylate III C19H18N4O4S have been synthesized and their structures determined by single crystal Xray crystallography I C14H11N3O4S is triclinic with space group P1 and cell constantsa = 773948 Å b = 12582611 Å c = 14728013 Å α = 772598° β = 758858° γ = 793428° V = 134362 Å3 Z = 4 II C18H19N3O4S is monoclinic with space group P21/c and cell constantsa = 1604995 Å b = 1201964 Å c = 978664 Å β = 1048794° V = 18246712 Å3 Z = 4 III C19H18N4O4S is triclinic with space group P1 and cell constants a = 903918 Å b = 10342912 Å c = 10814511 Å α = 758709° β = 714899° γ = 881118° V = 9286417 Å3 Z = 2 All three compounds have the same indole nitrogen phenylsulfonyl substituent In the crystals the dihedral angle between the mean planes of the pyrrolyl groups of the indole ring and phenylsulfonyl groups are 8608o IA or 8354o IB and 8506o III forming an Lshaped molecule while in II it is 5295o forming a Vshaped molecule due in part to the puckering of the pyrrolyl ring from the nonplanar indole group Additionally the DFT frontier molecular orbitals of each compound are displayed and correlation between the calculated molecular orbital energies eV for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound have been proposedSynthesis Crystal Structures Density Functional Theory DFT Calculations and Molecular Orbital Calculations of three new derivatives of 1phenylsulfonylindole 3nitro1phenylsulfonyl1Hindol2amine I C14H11N¬3O4S Ntertbutyl3nitro1phenylsulfonyl1Hindol2amine II C18H19N3O4S and tertbutyl 4phenylsulfonyl123triazolo45bindole14Hcarboxylate III C19H18N4O4S

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