A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine

S.H.M. Sontjens; J.T. Meijer; H. Kooijman; A.L. Spek; M.H.P. Genderen, van; R.P. Sijbesma; E.W. Meijer

doi:10.1021/ol016750a

A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine

S.H.M. Sontjens, J.T. Meijer, H. Kooijman, A.L. Spek, M.H.P. Genderen, van, R.P. Sijbesma, E.W. Meijer

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Abstract

A multiple hydrogen-bond array based on dipyrimidin-2-ylamine is presented, which is easily accessible. The influence of a preorganizing intramolecular hydrogen bond, tautomeric equilibria, and steric effects on the association behavior were investigated. X-ray diffraction shows that the molecules feature an ADA (acceptor-donor-acceptor) array of hydrogen-bonding sites in the solid state. The array persists in solution, and H-1 NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound.

Original language	English
Pages (from-to)	3887-3889
Journal	Organic Letters
Volume	3
Issue number	24
DOIs	https://doi.org/10.1021/ol016750a
Publication status	Published - 2001

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title = "A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine",

abstract = "A multiple hydrogen-bond array based on dipyrimidin-2-ylamine is presented, which is easily accessible. The influence of a preorganizing intramolecular hydrogen bond, tautomeric equilibria, and steric effects on the association behavior were investigated. X-ray diffraction shows that the molecules feature an ADA (acceptor-donor-acceptor) array of hydrogen-bonding sites in the solid state. The array persists in solution, and H-1 NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound.",

author = "S.H.M. Sontjens and J.T. Meijer and H. Kooijman and A.L. Spek and {Genderen, van}, M.H.P. and R.P. Sijbesma and E.W. Meijer",

year = "2001",

doi = "10.1021/ol016750a",

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journal = "Organic Letters",

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T1 - A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine

AU - Sontjens, S.H.M.

AU - Meijer, J.T.

AU - Kooijman, H.

AU - Spek, A.L.

AU - Genderen, van, M.H.P.

AU - Sijbesma, R.P.

AU - Meijer, E.W.

PY - 2001

Y1 - 2001

N2 - A multiple hydrogen-bond array based on dipyrimidin-2-ylamine is presented, which is easily accessible. The influence of a preorganizing intramolecular hydrogen bond, tautomeric equilibria, and steric effects on the association behavior were investigated. X-ray diffraction shows that the molecules feature an ADA (acceptor-donor-acceptor) array of hydrogen-bonding sites in the solid state. The array persists in solution, and H-1 NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound.

AB - A multiple hydrogen-bond array based on dipyrimidin-2-ylamine is presented, which is easily accessible. The influence of a preorganizing intramolecular hydrogen bond, tautomeric equilibria, and steric effects on the association behavior were investigated. X-ray diffraction shows that the molecules feature an ADA (acceptor-donor-acceptor) array of hydrogen-bonding sites in the solid state. The array persists in solution, and H-1 NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound.

U2 - 10.1021/ol016750a

DO - 10.1021/ol016750a

M3 - Article

SN - 1523-7060

VL - 3

SP - 3887

EP - 3889

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine

Abstract

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