The conformers of phenylglycine

Maria Eugenia Sanz; Vanessa Cortijo; W Caminati; JC Lopez; JL Alonso

doi:10.1002/chem.200501013

The conformers of phenylglycine

Maria Eugenia Sanz, Vanessa Cortijo, W Caminati, JC Lopez, JL Alonso^*

^*Corresponding author for this work

Chemistry

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

37 Citations (Scopus)

Abstract

The neutral form of the unnatural amino acid phenylglycine was vaporized by laser ablation, and the presence of two conformers was detected in a supersonic expansion by Fourier transform microwave spectroscopy. Both conformers were unequivocally identified by comparison of their experimental rotational and quadrupole coupling constants with those calculated ab initio. The most stable conformer is stabilized by intraniolecular hydrogen bonds N-(HO)-O-...=C N-H-...pi (with the closest C-C bond in the aromatic ring), and a cis-COOH interaction. The other conformer exhibits a O-(HN)-N-... hydrogen bond between the hydrogen atom of the hydroxyl group and the lone pair at the nitrogen atom.

Original language	English
Pages (from-to)	2564-2570
Number of pages	7
Journal	CHEMISTRY
Volume	12
Issue number	9
DOIs	https://doi.org/10.1002/chem.200501013
Publication status	Published - 8 Mar 2006

Keywords

ab initio calculations
amino acids
conformation analysis
hydrogen bonds
laser ablation
rotational spectroscopy
MILLIMETER-WAVE SPECTROSCOPY
EQUATORIAL HYDROGEN-BONDS
SEEDED SUPERSONIC JETS
AMINO-ACID TRYPTOPHAN
ION-DIP SPECTROSCOPY
GAS-PHASE
CONFORMATIONAL PREFERENCES
ROTATIONAL SPECTRUM
ELECTRONIC-SPECTRUM
MOLECULAR-BEAM

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10.1002/chem.200501013

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title = "The conformers of phenylglycine",

abstract = "The neutral form of the unnatural amino acid phenylglycine was vaporized by laser ablation, and the presence of two conformers was detected in a supersonic expansion by Fourier transform microwave spectroscopy. Both conformers were unequivocally identified by comparison of their experimental rotational and quadrupole coupling constants with those calculated ab initio. The most stable conformer is stabilized by intraniolecular hydrogen bonds N-(HO)-O-...=C N-H-...pi (with the closest C-C bond in the aromatic ring), and a cis-COOH interaction. The other conformer exhibits a O-(HN)-N-... hydrogen bond between the hydrogen atom of the hydroxyl group and the lone pair at the nitrogen atom.",

keywords = "ab initio calculations, amino acids, conformation analysis, hydrogen bonds, laser ablation, rotational spectroscopy, MILLIMETER-WAVE SPECTROSCOPY, EQUATORIAL HYDROGEN-BONDS, SEEDED SUPERSONIC JETS, AMINO-ACID TRYPTOPHAN, ION-DIP SPECTROSCOPY, GAS-PHASE, CONFORMATIONAL PREFERENCES, ROTATIONAL SPECTRUM, ELECTRONIC-SPECTRUM, MOLECULAR-BEAM",

author = "Sanz, {Maria Eugenia} and Vanessa Cortijo and W Caminati and JC Lopez and JL Alonso",

year = "2006",

month = mar,

day = "8",

doi = "10.1002/chem.200501013",

language = "English",

volume = "12",

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journal = "CHEMISTRY",

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TY - JOUR

T1 - The conformers of phenylglycine

AU - Sanz, Maria Eugenia

AU - Cortijo, Vanessa

AU - Caminati, W

AU - Lopez, JC

AU - Alonso, JL

PY - 2006/3/8

Y1 - 2006/3/8

N2 - The neutral form of the unnatural amino acid phenylglycine was vaporized by laser ablation, and the presence of two conformers was detected in a supersonic expansion by Fourier transform microwave spectroscopy. Both conformers were unequivocally identified by comparison of their experimental rotational and quadrupole coupling constants with those calculated ab initio. The most stable conformer is stabilized by intraniolecular hydrogen bonds N-(HO)-O-...=C N-H-...pi (with the closest C-C bond in the aromatic ring), and a cis-COOH interaction. The other conformer exhibits a O-(HN)-N-... hydrogen bond between the hydrogen atom of the hydroxyl group and the lone pair at the nitrogen atom.

AB - The neutral form of the unnatural amino acid phenylglycine was vaporized by laser ablation, and the presence of two conformers was detected in a supersonic expansion by Fourier transform microwave spectroscopy. Both conformers were unequivocally identified by comparison of their experimental rotational and quadrupole coupling constants with those calculated ab initio. The most stable conformer is stabilized by intraniolecular hydrogen bonds N-(HO)-O-...=C N-H-...pi (with the closest C-C bond in the aromatic ring), and a cis-COOH interaction. The other conformer exhibits a O-(HN)-N-... hydrogen bond between the hydrogen atom of the hydroxyl group and the lone pair at the nitrogen atom.

KW - ab initio calculations

KW - amino acids

KW - conformation analysis

KW - hydrogen bonds

KW - laser ablation

KW - rotational spectroscopy

KW - MILLIMETER-WAVE SPECTROSCOPY

KW - EQUATORIAL HYDROGEN-BONDS

KW - SEEDED SUPERSONIC JETS

KW - AMINO-ACID TRYPTOPHAN

KW - ION-DIP SPECTROSCOPY

KW - GAS-PHASE

KW - CONFORMATIONAL PREFERENCES

KW - ROTATIONAL SPECTRUM

KW - ELECTRONIC-SPECTRUM

KW - MOLECULAR-BEAM

U2 - 10.1002/chem.200501013

DO - 10.1002/chem.200501013

M3 - Article

SN - 0947-6539

VL - 12

SP - 2564

EP - 2570

JO - CHEMISTRY

JF - CHEMISTRY

IS - 9

ER -

The conformers of phenylglycine

Abstract

Keywords

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