Helical Folding of Alkanes in a Self-Assembled, Cylindrical Capsule

A. Scarso, Laurent Alain Claude Trembleau, J. Rebek Jnr

Research output: Contribution to journalArticle

124 Citations (Scopus)

Abstract

The reversible encapsulation of a series of normal alkane guests in a cylindrical host was studied by NMR methods. For small hydrocarbons such as n-pentane or n-hexane, two guests enter the host, and they move freely within. With n-heptane no encapsulation takes place. For longer alkanes such as n-decane, a single guest enters and the aromatic walls of the host are seen to twist to avoid empty spaces and increase favorable interactions with the hydrocarbon. The best guest (n-undecane) adopts a conformation with minimal gauche interactions. The longest alkane accommodated, n-tetradecane, adopts a helical conformation to fit in the cavity, a shape that maximizes CH/pi interactions with the aromatic walls of the receptor. These reciprocal conformational changes are discussed in terms of optimal host/guest interactions.

Original languageEnglish
Pages (from-to)13512-13518
Number of pages6
JournalJournal of the American Chemical Society
Volume126
DOIs
Publication statusPublished - 2004

Keywords

  • ENCAPSULATION COMPLEXES
  • MOLECULAR ENCAPSULATION
  • TEMPERATURE-DEPENDENCE
  • CHEMICAL-SHIFTS
  • RECOGNITION
  • ISOMERISM
  • PEPTIDES

Cite this

Helical Folding of Alkanes in a Self-Assembled, Cylindrical Capsule. / Scarso, A.; Trembleau, Laurent Alain Claude; Rebek Jnr, J.

In: Journal of the American Chemical Society, Vol. 126, 2004, p. 13512-13518.

Research output: Contribution to journalArticle

@article{0f9430fbf2c844cba892c258db0bc6d5,
title = "Helical Folding of Alkanes in a Self-Assembled, Cylindrical Capsule",
abstract = "The reversible encapsulation of a series of normal alkane guests in a cylindrical host was studied by NMR methods. For small hydrocarbons such as n-pentane or n-hexane, two guests enter the host, and they move freely within. With n-heptane no encapsulation takes place. For longer alkanes such as n-decane, a single guest enters and the aromatic walls of the host are seen to twist to avoid empty spaces and increase favorable interactions with the hydrocarbon. The best guest (n-undecane) adopts a conformation with minimal gauche interactions. The longest alkane accommodated, n-tetradecane, adopts a helical conformation to fit in the cavity, a shape that maximizes CH/pi interactions with the aromatic walls of the receptor. These reciprocal conformational changes are discussed in terms of optimal host/guest interactions.",
keywords = "ENCAPSULATION COMPLEXES, MOLECULAR ENCAPSULATION, TEMPERATURE-DEPENDENCE, CHEMICAL-SHIFTS, RECOGNITION, ISOMERISM, PEPTIDES",
author = "A. Scarso and Trembleau, {Laurent Alain Claude} and {Rebek Jnr}, J.",
year = "2004",
doi = "10.1021/ja047952f",
language = "English",
volume = "126",
pages = "13512--13518",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",

}

TY - JOUR

T1 - Helical Folding of Alkanes in a Self-Assembled, Cylindrical Capsule

AU - Scarso, A.

AU - Trembleau, Laurent Alain Claude

AU - Rebek Jnr, J.

PY - 2004

Y1 - 2004

N2 - The reversible encapsulation of a series of normal alkane guests in a cylindrical host was studied by NMR methods. For small hydrocarbons such as n-pentane or n-hexane, two guests enter the host, and they move freely within. With n-heptane no encapsulation takes place. For longer alkanes such as n-decane, a single guest enters and the aromatic walls of the host are seen to twist to avoid empty spaces and increase favorable interactions with the hydrocarbon. The best guest (n-undecane) adopts a conformation with minimal gauche interactions. The longest alkane accommodated, n-tetradecane, adopts a helical conformation to fit in the cavity, a shape that maximizes CH/pi interactions with the aromatic walls of the receptor. These reciprocal conformational changes are discussed in terms of optimal host/guest interactions.

AB - The reversible encapsulation of a series of normal alkane guests in a cylindrical host was studied by NMR methods. For small hydrocarbons such as n-pentane or n-hexane, two guests enter the host, and they move freely within. With n-heptane no encapsulation takes place. For longer alkanes such as n-decane, a single guest enters and the aromatic walls of the host are seen to twist to avoid empty spaces and increase favorable interactions with the hydrocarbon. The best guest (n-undecane) adopts a conformation with minimal gauche interactions. The longest alkane accommodated, n-tetradecane, adopts a helical conformation to fit in the cavity, a shape that maximizes CH/pi interactions with the aromatic walls of the receptor. These reciprocal conformational changes are discussed in terms of optimal host/guest interactions.

KW - ENCAPSULATION COMPLEXES

KW - MOLECULAR ENCAPSULATION

KW - TEMPERATURE-DEPENDENCE

KW - CHEMICAL-SHIFTS

KW - RECOGNITION

KW - ISOMERISM

KW - PEPTIDES

U2 - 10.1021/ja047952f

DO - 10.1021/ja047952f

M3 - Article

VL - 126

SP - 13512

EP - 13518

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

ER -