Conformational studies of dibenzo-16-crown-5 lariat ethers

Richard A. Bartsch; Jong Seung Kim; Uriel Olsher; David M. Purkiss

doi:10.1080/10610279608032551

Conformational studies of dibenzo-16-crown-5 lariat ethers

Richard A. Bartsch, Jong Seung Kim, Uriel Olsher, David M. Purkiss

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

8 Citations (Scopus)

Abstract

Conformations of sym-(R)(OR')dibenzo-16-crown-5 compounds with R = decyl and R' = H, CH₃, CH₂CO₂H, and CH₂CO₂CH₃, as well as R = alkyl, fluoroalkyl, alkenyl, and alkynyl and R' = CH₂CO₂H, in solution have been probed by NMR spectroscopy. The difference in chemical shifts of the diastereotopic hydrogens for the methylene groups adjacent to the geminally substituted ring carbon is utilized to assess the ease of inversion of the three-carbon bridges. For lariat ethers with R = C₁₀H₂₁, the chemical shift difference is much larger when R' = CH₂CO₂H and CH₂CO₂CH₃ than H and CH₃. In non-hydrogen bonding solvents, the chemical shift difference for lariat ethers with R = C₁₀H₂₁ is much larger when R' = CH₂CO₂H than CH₂CO₂CH₃ which demonstrates intramolecular hydrogen bonding of the carboxylic acid-containing side arm with a crown ether oxygen.

Original language	English
Pages (from-to)	327-331
Number of pages	5
Journal	Supramolecular Chemistry
Volume	6
Issue number	3-4
DOIs	https://doi.org/10.1080/10610279608032551
Publication status	Published - 1996
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by the Division of Chemical Sciences of the Office of Basic Energy Sciences of the U.S. Department of Energy (Grant DE-FG03-94ER14416).

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1080/10610279608032551

Cite this

@article{ef9d38b743ac43be94cbf22bc7e0ba67,

title = "Conformational studies of dibenzo-16-crown-5 lariat ethers",

abstract = "Conformations of sym-(R)(OR')dibenzo-16-crown-5 compounds with R = decyl and R' = H, CH3, CH2CO2H, and CH2CO2CH3, as well as R = alkyl, fluoroalkyl, alkenyl, and alkynyl and R' = CH2CO2H, in solution have been probed by NMR spectroscopy. The difference in chemical shifts of the diastereotopic hydrogens for the methylene groups adjacent to the geminally substituted ring carbon is utilized to assess the ease of inversion of the three-carbon bridges. For lariat ethers with R = C10H21, the chemical shift difference is much larger when R' = CH2CO2H and CH2CO2CH3 than H and CH3. In non-hydrogen bonding solvents, the chemical shift difference for lariat ethers with R = C10H21 is much larger when R' = CH2CO2H than CH2CO2CH3 which demonstrates intramolecular hydrogen bonding of the carboxylic acid-containing side arm with a crown ether oxygen.",

author = "Bartsch, {Richard A.} and Kim, {Jong Seung} and Uriel Olsher and Purkiss, {David M.}",

note = "Funding Information: This research was supported by the Division of Chemical Sciences of the Office of Basic Energy Sciences of the U.S. Department of Energy (Grant DE-FG03-94ER14416).",

year = "1996",

doi = "10.1080/10610279608032551",

language = "English",

volume = "6",

pages = "327--331",

journal = "Supramolecular Chemistry",

issn = "1061-0278",

publisher = "Taylor and Francis Ltd.",

number = "3-4",

}

TY - JOUR

T1 - Conformational studies of dibenzo-16-crown-5 lariat ethers

AU - Bartsch, Richard A.

AU - Kim, Jong Seung

AU - Olsher, Uriel

AU - Purkiss, David M.

N1 - Funding Information: This research was supported by the Division of Chemical Sciences of the Office of Basic Energy Sciences of the U.S. Department of Energy (Grant DE-FG03-94ER14416).

PY - 1996

Y1 - 1996

N2 - Conformations of sym-(R)(OR')dibenzo-16-crown-5 compounds with R = decyl and R' = H, CH3, CH2CO2H, and CH2CO2CH3, as well as R = alkyl, fluoroalkyl, alkenyl, and alkynyl and R' = CH2CO2H, in solution have been probed by NMR spectroscopy. The difference in chemical shifts of the diastereotopic hydrogens for the methylene groups adjacent to the geminally substituted ring carbon is utilized to assess the ease of inversion of the three-carbon bridges. For lariat ethers with R = C10H21, the chemical shift difference is much larger when R' = CH2CO2H and CH2CO2CH3 than H and CH3. In non-hydrogen bonding solvents, the chemical shift difference for lariat ethers with R = C10H21 is much larger when R' = CH2CO2H than CH2CO2CH3 which demonstrates intramolecular hydrogen bonding of the carboxylic acid-containing side arm with a crown ether oxygen.

AB - Conformations of sym-(R)(OR')dibenzo-16-crown-5 compounds with R = decyl and R' = H, CH3, CH2CO2H, and CH2CO2CH3, as well as R = alkyl, fluoroalkyl, alkenyl, and alkynyl and R' = CH2CO2H, in solution have been probed by NMR spectroscopy. The difference in chemical shifts of the diastereotopic hydrogens for the methylene groups adjacent to the geminally substituted ring carbon is utilized to assess the ease of inversion of the three-carbon bridges. For lariat ethers with R = C10H21, the chemical shift difference is much larger when R' = CH2CO2H and CH2CO2CH3 than H and CH3. In non-hydrogen bonding solvents, the chemical shift difference for lariat ethers with R = C10H21 is much larger when R' = CH2CO2H than CH2CO2CH3 which demonstrates intramolecular hydrogen bonding of the carboxylic acid-containing side arm with a crown ether oxygen.

UR - http://www.scopus.com/inward/record.url?scp=0002152376&partnerID=8YFLogxK

U2 - 10.1080/10610279608032551

DO - 10.1080/10610279608032551

M3 - Article

AN - SCOPUS:0002152376

SN - 1061-0278

VL - 6

SP - 327

EP - 331

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 3-4

ER -

Conformational studies of dibenzo-16-crown-5 lariat ethers

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this