Bis(benzimidazolium)methane salts: A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes

Sabari Ghosh; Ann Marie Schmiedekamp; Chhanda Mukhopadhyay

doi:10.1016/j.tet.2012.08.080

Bis(benzimidazolium)methane salts: A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes

Sabari Ghosh, Ann Marie Schmiedekamp, Chhanda Mukhopadhyay

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by ¹H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O ₁⋯O _4′ and O ₃⋯O _2′ across the dibenzo axis of the crown.

Original language	English (US)
Pages (from-to)	9826-9835
Number of pages	10
Journal	Tetrahedron
Volume	68
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2012.08.080
State	Published - Nov 25 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.08.080

Fingerprint Dive into the research topics of 'Bis(benzimidazolium)methane salts: A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes'. Together they form a unique fingerprint.

Cite this

@article{b83c75912bba4ffcbbed0db8b53c1d57,

title = "Bis(benzimidazolium)methane salts: A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes",

abstract = "We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by 1H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O 1⋯O 4′ and O 3⋯O 2′ across the dibenzo axis of the crown.",

author = "Sabari Ghosh and Schmiedekamp, {Ann Marie} and Chhanda Mukhopadhyay",

year = "2012",

month = nov,

day = "25",

doi = "10.1016/j.tet.2012.08.080",

language = "English (US)",

volume = "68",

pages = "9826--9835",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "47",

}

TY - JOUR

T1 - Bis(benzimidazolium)methane salts

T2 - A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes

AU - Ghosh, Sabari

AU - Schmiedekamp, Ann Marie

AU - Mukhopadhyay, Chhanda

PY - 2012/11/25

Y1 - 2012/11/25

N2 - We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by 1H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O 1⋯O 4′ and O 3⋯O 2′ across the dibenzo axis of the crown.

AB - We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by 1H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O 1⋯O 4′ and O 3⋯O 2′ across the dibenzo axis of the crown.

UR - http://www.scopus.com/inward/record.url?scp=84867508779&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84867508779&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.08.080

DO - 10.1016/j.tet.2012.08.080

M3 - Article

AN - SCOPUS:84867508779

VL - 68

SP - 9826

EP - 9835

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 47

ER -