Comparison Crystal Structure Conformations of Two Structurally Related Biphenyl Analogues: 4,4'-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and 4,4'-bis{3-[(S)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl

Authors

Anqi Wan, University of Arkansas for Medical Sciences
Narsimha Reddy Penthala, University of Arkansas for Medical Sciences
E. Kim Fifer, University of Arkansas for Medical Sciences
Sean Parkin, University of KentuckyFollow
Peter A. Crooks, University of Arkansas for Medical Sciences

Abstract

The title compounds, C₂₆H₂₈N₂, (I), and C₂₈H₃₂N₂, (II), were designed based on the structure of the potent 910 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1'-[[1,1'-biphen­yl]-4,4'-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bromide}. In order to improve the druglikeness properties of ZZ161C for potential oral administration, the title compounds (I) and (II) were prepared by coupling 4,4'-bis­(3-bromo­prop-1-yn-1-yl)-1,1'-biphenyl with pyrrol­idine, (I), and (S)-2-methyl­pyrrolidine, (II), respectively, in aceto­nitrile at room temperature. The asymmetric unit of (I) contains two half mol­ecules that each sit on sites of crystallographic inversion. As a result, the biphenyl ring systems in compound (I) are coplanar. The biphenyl ring system in compound (II), however, has a dihedral angle of 28.76 (11)°. In (I), the two independent mol­ecules differ in the orientation of the pyrrolidine ring (the nitro­gen lone pair points towards the biphenyl rings in one mol­ecule, but away from the rings in the other). The torsion angles about the ethynyl groups between the planes of the phenyl rings and the pyrrolidine ring N atoms are 84.15 (10) and -152.89 (10)°. In compound (II), the corresponding torsion angles are 122.0 (3) and 167.0 (3)°, with the nitro­gen lone pairs at both ends of the mol­ecule directed away from the central biphenyl rings.

Document Type

Article

Publication Date

10-2015

Notes/Citation Information

Published in Acta Crystallographica Section E: Cystallographic Communications, v. 71, part 10, p. 1147-1150.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Digital Object Identifier (DOI)

https://doi.org/10.1107/S2056989015016163

Funding Information

This investigation was supported by ARA (Arkansas Research Alliance).

Related Content

CCDC references: 1421219; 1421218

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S2056989015016163/hg5457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016163/hg5457Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S2056989015016163/hg5457IIsup3.hkl

Supporting information file. DOI: 10.1107/S2056989015016163/hg5457Isup4.cml

Supporting information file. DOI: 10.1107/S2056989015016163/hg5457IIsup5.cml

checkCIF report

3D view of crystallographic information

Repository Citation

Wan, Anqi; Penthala, Narsimha Reddy; Fifer, E. Kim; Parkin, Sean; and Crooks, Peter A., "Comparison Crystal Structure Conformations of Two Structurally Related Biphenyl Analogues: 4,4'-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and 4,4'-bis{3-[(S)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl" (2015). Chemistry Faculty Publications. 65.
https://uknowledge.uky.edu/chemistry_facpub/65