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

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

26 Citations (Scopus)

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

Access to Document

10.1021/ol016750a

Cite this

@article{e8014dfc124943d7aa43b55f9f1a8556,

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",

language = "English",

volume = "3",

pages = "3887--3889",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

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

Access to Document

Fingerprint

Cite this