Expanding cavitand chemistry: The preparation and characterization of [n]cavitands with n ≥ 4

Christoph Naumann, Esteban Román, Carlos Peinador, Tong Ren, Brian O. Patrick, Angel Kaifer, John C. Sherman

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n=4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n=6 and 7) adopt conformations of lower symmetry, 1H NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5] cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.

Original languageEnglish (US)
Pages (from-to)1637-1645
Number of pages9
JournalChemistry - A European Journal
Volume7
Issue number8
DOIs
StatePublished - Apr 17 2001

Fingerprint

Conformations
Cones
Molecular mechanics
Nuclear magnetic resonance
Single crystals
X ray diffraction
cavitand
Temperature

Keywords

  • Cavitands
  • Chemical exchange
  • Host-guest chemistry
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Expanding cavitand chemistry : The preparation and characterization of [n]cavitands with n ≥ 4. / Naumann, Christoph; Román, Esteban; Peinador, Carlos; Ren, Tong; Patrick, Brian O.; Kaifer, Angel; Sherman, John C.

In: Chemistry - A European Journal, Vol. 7, No. 8, 17.04.2001, p. 1637-1645.

Research output: Contribution to journalArticle

Naumann, Christoph ; Román, Esteban ; Peinador, Carlos ; Ren, Tong ; Patrick, Brian O. ; Kaifer, Angel ; Sherman, John C. / Expanding cavitand chemistry : The preparation and characterization of [n]cavitands with n ≥ 4. In: Chemistry - A European Journal. 2001 ; Vol. 7, No. 8. pp. 1637-1645.
@article{4b356ce1d7e0448287cb43e6fcf11789,
title = "Expanding cavitand chemistry: The preparation and characterization of [n]cavitands with n ≥ 4",
abstract = "The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n=4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n=6 and 7) adopt conformations of lower symmetry, 1H NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5] cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.",
keywords = "Cavitands, Chemical exchange, Host-guest chemistry, Supramolecular chemistry",
author = "Christoph Naumann and Esteban Rom{\'a}n and Carlos Peinador and Tong Ren and Patrick, {Brian O.} and Angel Kaifer and Sherman, {John C.}",
year = "2001",
month = "4",
day = "17",
doi = "10.1002/1521-3765(20010417)7:8<1637::AID-CHEM16370>3.0.CO;2-X",
language = "English (US)",
volume = "7",
pages = "1637--1645",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "8",

}

TY - JOUR

T1 - Expanding cavitand chemistry

T2 - The preparation and characterization of [n]cavitands with n ≥ 4

AU - Naumann, Christoph

AU - Román, Esteban

AU - Peinador, Carlos

AU - Ren, Tong

AU - Patrick, Brian O.

AU - Kaifer, Angel

AU - Sherman, John C.

PY - 2001/4/17

Y1 - 2001/4/17

N2 - The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n=4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n=6 and 7) adopt conformations of lower symmetry, 1H NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5] cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.

AB - The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n=4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n=6 and 7) adopt conformations of lower symmetry, 1H NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5] cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.

KW - Cavitands

KW - Chemical exchange

KW - Host-guest chemistry

KW - Supramolecular chemistry

UR - http://www.scopus.com/inward/record.url?scp=0035901677&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035901677&partnerID=8YFLogxK

U2 - 10.1002/1521-3765(20010417)7:8<1637::AID-CHEM16370>3.0.CO;2-X

DO - 10.1002/1521-3765(20010417)7:8<1637::AID-CHEM16370>3.0.CO;2-X

M3 - Article

C2 - 11349904

AN - SCOPUS:0035901677

VL - 7

SP - 1637

EP - 1645

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 8

ER -