Macrocyclic Receptor Molecules for Guanidinium Cations. 2. Synthesis and X-Ray Structures of 2,6-Pyrido Crown Ethers and their Guanidinium Complexes

Jos W H M Uiterwijk; Catherina J Van Staveren; David N Reinhoudt; Herman J Den Hertog  Jr.; Laminus Kruise; Sybolt Harkema

doi:10.1021/jo00359a037

Macrocyclic Receptor Molecules for Guanidinium Cations. 2. Synthesis and X-Ray Structures of 2,6-Pyrido Crown Ethers and their Guanidinium Complexes

Jos W H M Uiterwijk, Catherina J Van Staveren, David N Reinhoudt, Herman J Den Hertog Jr., Laminus Kruise, Sybolt Harkema

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

Abstract

2,6-Pyrido crown ethers I (n = 0-6) were synthesized and their complexation with guanidinium salts studied by using two phase extn. expts. The crystal and mol. structures of the complexes and the free 2,6-pyrido-24-crown-8 were detd. by x-ray crystallog. In the free and protonated crown ethers, the cavity is occupied by the arom. ring of the crown ether. In the complexes with guanidinium salts the guest mol. is encapsulated within the cavity, using all its hydrogen atoms for H-bonding between host and guest. The best fit for the guanidinium ion is found for the 27-membered macrocycle with a complementary host-guest H-bonding scheme. Crown ethers with 18 ring atoms form perching complexes.

Original language	English
Pages (from-to)	1575-1587
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	51
Issue number	9
DOIs	https://doi.org/10.1021/jo00359a037
Publication status	Published - 1986
Externally published	Yes

Keywords

Crown compounds Role: SPN (Synthetic preparation),
Crystal structure
Molecular structure (of pyrido crown ether-guanidi
complexation pyrido crown ether
crystal structure pyrido crown ether
guanidinium pyrido crown ether
mol structure pyrido crown ether
x ray pyrido crown ether

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10.1021/jo00359a037

http://www.mendeley.com/research/macrocyclic-receptor-molecules-guanidinium-cations-2-synthesis-xray-structures-26pyrido-crown-ethers

Cite this

@article{1e35307e999f46b19bfae66de55b4ed5,

title = "Macrocyclic Receptor Molecules for Guanidinium Cations. 2. Synthesis and X-Ray Structures of 2,6-Pyrido Crown Ethers and their Guanidinium Complexes",

abstract = "2,6-Pyrido crown ethers I (n = 0-6) were synthesized and their complexation with guanidinium salts studied by using two phase extn. expts. The crystal and mol. structures of the complexes and the free 2,6-pyrido-24-crown-8 were detd. by x-ray crystallog. In the free and protonated crown ethers, the cavity is occupied by the arom. ring of the crown ether. In the complexes with guanidinium salts the guest mol. is encapsulated within the cavity, using all its hydrogen atoms for H-bonding between host and guest. The best fit for the guanidinium ion is found for the 27-membered macrocycle with a complementary host-guest H-bonding scheme. Crown ethers with 18 ring atoms form perching complexes.",

keywords = "Crown compounds Role: SPN (Synthetic preparation),, Crystal structure, Molecular structure (of pyrido crown ether-guanidi, complexation pyrido crown ether, crystal structure pyrido crown ether, guanidinium pyrido crown ether, mol structure pyrido crown ether, x ray pyrido crown ether",

author = "Uiterwijk, {Jos W H M} and {Van Staveren}, {Catherina J} and Reinhoudt, {David N} and {Den Hertog Jr.}, {Herman J} and Laminus Kruise and Sybolt Harkema",

year = "1986",

doi = "10.1021/jo00359a037",

language = "English",

volume = "51",

pages = "1575--1587",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

Macrocyclic Receptor Molecules for Guanidinium Cations. 2. Synthesis and X-Ray Structures of 2,6-Pyrido Crown Ethers and their Guanidinium Complexes. / Uiterwijk, Jos W H M; Van Staveren, Catherina J; Reinhoudt, David N et al.
In: Journal of Organic Chemistry, Vol. 51, No. 9, 1986, p. 1575-1587.

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

TY - JOUR

T1 - Macrocyclic Receptor Molecules for Guanidinium Cations. 2. Synthesis and X-Ray Structures of 2,6-Pyrido Crown Ethers and their Guanidinium Complexes

AU - Uiterwijk, Jos W H M

AU - Van Staveren, Catherina J

AU - Reinhoudt, David N

AU - Den Hertog Jr., Herman J

AU - Kruise, Laminus

AU - Harkema, Sybolt

PY - 1986

Y1 - 1986

N2 - 2,6-Pyrido crown ethers I (n = 0-6) were synthesized and their complexation with guanidinium salts studied by using two phase extn. expts. The crystal and mol. structures of the complexes and the free 2,6-pyrido-24-crown-8 were detd. by x-ray crystallog. In the free and protonated crown ethers, the cavity is occupied by the arom. ring of the crown ether. In the complexes with guanidinium salts the guest mol. is encapsulated within the cavity, using all its hydrogen atoms for H-bonding between host and guest. The best fit for the guanidinium ion is found for the 27-membered macrocycle with a complementary host-guest H-bonding scheme. Crown ethers with 18 ring atoms form perching complexes.

AB - 2,6-Pyrido crown ethers I (n = 0-6) were synthesized and their complexation with guanidinium salts studied by using two phase extn. expts. The crystal and mol. structures of the complexes and the free 2,6-pyrido-24-crown-8 were detd. by x-ray crystallog. In the free and protonated crown ethers, the cavity is occupied by the arom. ring of the crown ether. In the complexes with guanidinium salts the guest mol. is encapsulated within the cavity, using all its hydrogen atoms for H-bonding between host and guest. The best fit for the guanidinium ion is found for the 27-membered macrocycle with a complementary host-guest H-bonding scheme. Crown ethers with 18 ring atoms form perching complexes.

KW - Crown compounds Role: SPN (Synthetic preparation),

KW - Crystal structure

KW - Molecular structure (of pyrido crown ether-guanidi

KW - complexation pyrido crown ether

KW - crystal structure pyrido crown ether

KW - guanidinium pyrido crown ether

KW - mol structure pyrido crown ether

KW - x ray pyrido crown ether

U2 - 10.1021/jo00359a037

DO - 10.1021/jo00359a037

M3 - Article

SN - 0022-3263

VL - 51

SP - 1575

EP - 1587

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -