Enantiomeric recognition by chiral pyridino-18-crown-6 for 1-naphthylethylamine. The effect of alkyl substituents on the macrocycle ring

Jon K. Hathaway, Reed M. Izatt, Jerald S. Bradshaw, Cheng Y. Zhu, P. Huszthy

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Molecular recognition of three chiral pyridino-18-crown-6 macrocycles with various dialkyl substituents for (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) has been determined by isoperibol titration calorimetry and compared to values already determined for the chiral di-methyl- and di-tert-butyl-sub-stituted crowns. Possible mechanisms of recognition for these systems are discussed using the thermodynamic values log K, ΔH, and TΔS. Macrocycles with the bulky substituents tert-butyl, isobutyl, and sec-butyl showed better recognition than those with the less bulky isopropyl and methyl substituents. In the case of macrocycles with bulky substituents, recognition of the enantiomers of NapEt was mainly the result of differences in entropy value changes. With macrocycles having less bulky substituents, reognition was mainly the result of differences in enthalpy value changes.

Original languageEnglish
Pages (from-to)9-13
Number of pages5
JournalSupramolecular Chemistry
Volume5
Issue number1
DOIs
Publication statusPublished - May 1 1995

Fingerprint

Molecular recognition
Enantiomers
Calorimetry
Titration
Enthalpy
Entropy
Thermodynamics
ammonium perchlorate
18-crown-6

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantiomeric recognition by chiral pyridino-18-crown-6 for 1-naphthylethylamine. The effect of alkyl substituents on the macrocycle ring. / Hathaway, Jon K.; Izatt, Reed M.; Bradshaw, Jerald S.; Zhu, Cheng Y.; Huszthy, P.

In: Supramolecular Chemistry, Vol. 5, No. 1, 01.05.1995, p. 9-13.

Research output: Contribution to journalArticle

@article{e341ecd0bfe3418390d5b270963f4540,
title = "Enantiomeric recognition by chiral pyridino-18-crown-6 for 1-naphthylethylamine. The effect of alkyl substituents on the macrocycle ring",
abstract = "Molecular recognition of three chiral pyridino-18-crown-6 macrocycles with various dialkyl substituents for (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) has been determined by isoperibol titration calorimetry and compared to values already determined for the chiral di-methyl- and di-tert-butyl-sub-stituted crowns. Possible mechanisms of recognition for these systems are discussed using the thermodynamic values log K, ΔH, and TΔS. Macrocycles with the bulky substituents tert-butyl, isobutyl, and sec-butyl showed better recognition than those with the less bulky isopropyl and methyl substituents. In the case of macrocycles with bulky substituents, recognition of the enantiomers of NapEt was mainly the result of differences in entropy value changes. With macrocycles having less bulky substituents, reognition was mainly the result of differences in enthalpy value changes.",
author = "Hathaway, {Jon K.} and Izatt, {Reed M.} and Bradshaw, {Jerald S.} and Zhu, {Cheng Y.} and P. Huszthy",
year = "1995",
month = "5",
day = "1",
doi = "10.1080/10610279508029881",
language = "English",
volume = "5",
pages = "9--13",
journal = "Supramolecular Chemistry",
issn = "1061-0278",
publisher = "Taylor and Francis Ltd.",
number = "1",

}

TY - JOUR

T1 - Enantiomeric recognition by chiral pyridino-18-crown-6 for 1-naphthylethylamine. The effect of alkyl substituents on the macrocycle ring

AU - Hathaway, Jon K.

AU - Izatt, Reed M.

AU - Bradshaw, Jerald S.

AU - Zhu, Cheng Y.

AU - Huszthy, P.

PY - 1995/5/1

Y1 - 1995/5/1

N2 - Molecular recognition of three chiral pyridino-18-crown-6 macrocycles with various dialkyl substituents for (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) has been determined by isoperibol titration calorimetry and compared to values already determined for the chiral di-methyl- and di-tert-butyl-sub-stituted crowns. Possible mechanisms of recognition for these systems are discussed using the thermodynamic values log K, ΔH, and TΔS. Macrocycles with the bulky substituents tert-butyl, isobutyl, and sec-butyl showed better recognition than those with the less bulky isopropyl and methyl substituents. In the case of macrocycles with bulky substituents, recognition of the enantiomers of NapEt was mainly the result of differences in entropy value changes. With macrocycles having less bulky substituents, reognition was mainly the result of differences in enthalpy value changes.

AB - Molecular recognition of three chiral pyridino-18-crown-6 macrocycles with various dialkyl substituents for (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) has been determined by isoperibol titration calorimetry and compared to values already determined for the chiral di-methyl- and di-tert-butyl-sub-stituted crowns. Possible mechanisms of recognition for these systems are discussed using the thermodynamic values log K, ΔH, and TΔS. Macrocycles with the bulky substituents tert-butyl, isobutyl, and sec-butyl showed better recognition than those with the less bulky isopropyl and methyl substituents. In the case of macrocycles with bulky substituents, recognition of the enantiomers of NapEt was mainly the result of differences in entropy value changes. With macrocycles having less bulky substituents, reognition was mainly the result of differences in enthalpy value changes.

UR - http://www.scopus.com/inward/record.url?scp=84972994868&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84972994868&partnerID=8YFLogxK

U2 - 10.1080/10610279508029881

DO - 10.1080/10610279508029881

M3 - Article

AN - SCOPUS:84972994868

VL - 5

SP - 9

EP - 13

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

SN - 1061-0278

IS - 1

ER -