Chip-based on-line nanospray MS method enabling study of the kinetics of isocyanate derivatization reactions

Monica Brivio; Andre Liesener; R. Edwin Oosterbroek; Willem Verboom; Uwe Karst; Albert van den Berg; David N. Reinhoudt

doi:10.1021/ac050817g

Chip-based on-line nanospray MS method enabling study of the kinetics of isocyanate derivatization reactions

Monica Brivio, Andre Liesener, R. Edwin Oosterbroek, Willem Verboom, Uwe Karst, Albert van den Berg, David N. Reinhoudt

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Abstract

The reaction of propyl isocyanate (2), benzyl isocyanate (3), and toluene-2,4-diisocyanate (4) with 4-nitro-7-piperazino-2,1,3-benzoxadiazole (1) to yield the corresponding urea derivatives 5 was carried out in a continuous flow glass microfluidics chip. Real-time monitoring of the derivatization reactions was done by electrospray ionization mass spectrometry, making use of a recently reported modular chip-MS interface. Rate constants of 1.5 × 104, 5.2 × 104, and 2.4 × 104 M-1 min-1 were determined for 2, 3, and 4, respectively. Using macroscale batch conditions, the rate constants are 3-4 times lower. The faster on-chip kinetics is attributed to the more efficient molecular diffusion in the micrometer-sized channel.

Original language	English
Pages (from-to)	6852-6856
Number of pages	5
Journal	Analytical chemistry
Volume	77
Issue number	21
DOIs	https://doi.org/10.1021/ac050817g
Publication status	Published - 2005

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@article{db32c482332142cc92dda8552ea932a6,

title = "Chip-based on-line nanospray MS method enabling study of the kinetics of isocyanate derivatization reactions",

abstract = "The reaction of propyl isocyanate (2), benzyl isocyanate (3), and toluene-2,4-diisocyanate (4) with 4-nitro-7-piperazino-2,1,3-benzoxadiazole (1) to yield the corresponding urea derivatives 5 was carried out in a continuous flow glass microfluidics chip. Real-time monitoring of the derivatization reactions was done by electrospray ionization mass spectrometry, making use of a recently reported modular chip-MS interface. Rate constants of 1.5 × 104, 5.2 × 104, and 2.4 × 104 M-1 min-1 were determined for 2, 3, and 4, respectively. Using macroscale batch conditions, the rate constants are 3-4 times lower. The faster on-chip kinetics is attributed to the more efficient molecular diffusion in the micrometer-sized channel.",

author = "Monica Brivio and Andre Liesener and Oosterbroek, {R. Edwin} and Willem Verboom and Uwe Karst and {van den Berg}, Albert and Reinhoudt, {David N.}",

note = "The authors thank the Micro Chemical Systems (MiCS) scientific program of the MESA+ Institute for Nanotechnology and the University of Twente for financial support.",

year = "2005",

doi = "10.1021/ac050817g",

language = "English",

volume = "77",

pages = "6852--6856",

journal = "Analytical chemistry",

issn = "0003-2700",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Chip-based on-line nanospray MS method enabling study of the kinetics of isocyanate derivatization reactions

AU - Brivio, Monica

AU - Liesener, Andre

AU - Oosterbroek, R. Edwin

AU - Verboom, Willem

AU - Karst, Uwe

AU - van den Berg, Albert

AU - Reinhoudt, David N.

N1 - The authors thank the Micro Chemical Systems (MiCS) scientific program of the MESA+ Institute for Nanotechnology and the University of Twente for financial support.

PY - 2005

Y1 - 2005

N2 - The reaction of propyl isocyanate (2), benzyl isocyanate (3), and toluene-2,4-diisocyanate (4) with 4-nitro-7-piperazino-2,1,3-benzoxadiazole (1) to yield the corresponding urea derivatives 5 was carried out in a continuous flow glass microfluidics chip. Real-time monitoring of the derivatization reactions was done by electrospray ionization mass spectrometry, making use of a recently reported modular chip-MS interface. Rate constants of 1.5 × 104, 5.2 × 104, and 2.4 × 104 M-1 min-1 were determined for 2, 3, and 4, respectively. Using macroscale batch conditions, the rate constants are 3-4 times lower. The faster on-chip kinetics is attributed to the more efficient molecular diffusion in the micrometer-sized channel.

AB - The reaction of propyl isocyanate (2), benzyl isocyanate (3), and toluene-2,4-diisocyanate (4) with 4-nitro-7-piperazino-2,1,3-benzoxadiazole (1) to yield the corresponding urea derivatives 5 was carried out in a continuous flow glass microfluidics chip. Real-time monitoring of the derivatization reactions was done by electrospray ionization mass spectrometry, making use of a recently reported modular chip-MS interface. Rate constants of 1.5 × 104, 5.2 × 104, and 2.4 × 104 M-1 min-1 were determined for 2, 3, and 4, respectively. Using macroscale batch conditions, the rate constants are 3-4 times lower. The faster on-chip kinetics is attributed to the more efficient molecular diffusion in the micrometer-sized channel.

U2 - 10.1021/ac050817g

DO - 10.1021/ac050817g

M3 - Article

SN - 0003-2700

VL - 77

SP - 6852

EP - 6856

JO - Analytical chemistry

JF - Analytical chemistry

IS - 21

ER -

Chip-based on-line nanospray MS method enabling study of the kinetics of isocyanate derivatization reactions

Abstract

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