Reactivity in monolayers versus bulk media: Intra- and intermolecular aminolysis of esters

V  Chechik; C J M  Stirling

Reactivity in monolayers versus bulk media: Intra- and intermolecular aminolysis of esters

V Chechik, C J M Stirling

Chemistry

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

Abstract

Monolayers possessing reactive amino and p-nitrophenyl ester functional groups at the same or different levels with respect to the monolayer interface have been self-assembled on a gold surface. Intramolecular reactions in these monolayers are at least 1000 times slower than the same processes in the bulk medium. Control experiments with external reagents showed that the monolayer p-nitrophenyl ester group reacts readily with amines from solution, whereas nucleophilicity of the monolayer amino functionality is significantly suppressed. This unusually low reactivity of the amino group was tentatively assigned to its interaction with the gold surface.

Original language	English
Pages (from-to)	6354-6356
Number of pages	3
Journal	Langmuir
Volume	13
Issue number	24
Publication status	Published - 26 Nov 1997

Keywords

SELF-ASSEMBLED MONOLAYERS
GOLD
SPECTROSCOPY
SURFACES
THIOLS

Cite this

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title = "Reactivity in monolayers versus bulk media: Intra- and intermolecular aminolysis of esters",

abstract = "Monolayers possessing reactive amino and p-nitrophenyl ester functional groups at the same or different levels with respect to the monolayer interface have been self-assembled on a gold surface. Intramolecular reactions in these monolayers are at least 1000 times slower than the same processes in the bulk medium. Control experiments with external reagents showed that the monolayer p-nitrophenyl ester group reacts readily with amines from solution, whereas nucleophilicity of the monolayer amino functionality is significantly suppressed. This unusually low reactivity of the amino group was tentatively assigned to its interaction with the gold surface.",

keywords = "SELF-ASSEMBLED MONOLAYERS, GOLD, SPECTROSCOPY, SURFACES, THIOLS",

author = "V Chechik and Stirling, {C J M}",

year = "1997",

month = nov,

day = "26",

language = "English",

volume = "13",

pages = "6354--6356",

journal = "Langmuir",

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publisher = "American Chemical Society",

number = "24",

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TY - JOUR

T1 - Reactivity in monolayers versus bulk media: Intra- and intermolecular aminolysis of esters

AU - Chechik, V

AU - Stirling, C J M

PY - 1997/11/26

Y1 - 1997/11/26

N2 - Monolayers possessing reactive amino and p-nitrophenyl ester functional groups at the same or different levels with respect to the monolayer interface have been self-assembled on a gold surface. Intramolecular reactions in these monolayers are at least 1000 times slower than the same processes in the bulk medium. Control experiments with external reagents showed that the monolayer p-nitrophenyl ester group reacts readily with amines from solution, whereas nucleophilicity of the monolayer amino functionality is significantly suppressed. This unusually low reactivity of the amino group was tentatively assigned to its interaction with the gold surface.

AB - Monolayers possessing reactive amino and p-nitrophenyl ester functional groups at the same or different levels with respect to the monolayer interface have been self-assembled on a gold surface. Intramolecular reactions in these monolayers are at least 1000 times slower than the same processes in the bulk medium. Control experiments with external reagents showed that the monolayer p-nitrophenyl ester group reacts readily with amines from solution, whereas nucleophilicity of the monolayer amino functionality is significantly suppressed. This unusually low reactivity of the amino group was tentatively assigned to its interaction with the gold surface.

KW - SELF-ASSEMBLED MONOLAYERS

KW - GOLD

KW - SPECTROSCOPY

KW - SURFACES

KW - THIOLS

M3 - Letter

SN - 0743-7463

VL - 13

SP - 6354

EP - 6356

JO - Langmuir

JF - Langmuir

IS - 24

ER -