Reactivity of N-nitrosoamides in confined spaces

Aaron C. Sather; Orion B. Berryman; Dariush Ajami; Julius Rebek

doi:10.1016/j.tetlet.2010.11.030

Reactivity of N-nitrosoamides in confined spaces

Aaron C. Sather, Orion B. Berryman, Dariush Ajami, Julius Rebek

Chemistry

Scripps Research Institute

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

15 Scopus citations

Abstract

The thermal rearrangement of several N-nitrosoamides was studied by ¹H NMR in the context of reversible encapsulation. The N-nitrosoamide guests were isolated from the bulk solvent in a hydrogen-bonded dimeric host capsule which prevented their rearrangement. The guests appear to be preserved in their ground state conformations by the pressure exerted by the host. The conformations of the free and bound N-nitrosoamides are of comparable relative energies as determined by DFT calculations.

Original language	English
Pages (from-to)	2100-2103
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.030
State	Published - Apr 27 2011

Keywords

Hydrogen bonding
N-Nitrosoamides
Reversible encapsulation

Access to Document

10.1016/j.tetlet.2010.11.030

Cite this

@article{2f6af11a9e514501ac57c9f886d2abdf,

title = "Reactivity of N-nitrosoamides in confined spaces",

abstract = "The thermal rearrangement of several N-nitrosoamides was studied by 1H NMR in the context of reversible encapsulation. The N-nitrosoamide guests were isolated from the bulk solvent in a hydrogen-bonded dimeric host capsule which prevented their rearrangement. The guests appear to be preserved in their ground state conformations by the pressure exerted by the host. The conformations of the free and bound N-nitrosoamides are of comparable relative energies as determined by DFT calculations.",

keywords = "Hydrogen bonding, N-Nitrosoamides, Reversible encapsulation",

author = "Sather, {Aaron C.} and Berryman, {Orion B.} and Dariush Ajami and Julius Rebek",

note = "Funding Information: We are grateful to the Skaggs Institute for support. A.C.S. is a Skaggs Pre-doctoral Fellow. O.B.B. thanks the NIGMS (GM 27953) for financial support. A postdoctoral fellowship for O.B.B. was provided by NIH (F32GM087068). ",

year = "2011",

month = apr,

day = "27",

doi = "10.1016/j.tetlet.2010.11.030",

language = "English",

volume = "52",

pages = "2100--2103",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "17",

}

TY - JOUR

T1 - Reactivity of N-nitrosoamides in confined spaces

AU - Sather, Aaron C.

AU - Berryman, Orion B.

AU - Ajami, Dariush

AU - Rebek, Julius

N1 - Funding Information: We are grateful to the Skaggs Institute for support. A.C.S. is a Skaggs Pre-doctoral Fellow. O.B.B. thanks the NIGMS (GM 27953) for financial support. A postdoctoral fellowship for O.B.B. was provided by NIH (F32GM087068).

PY - 2011/4/27

Y1 - 2011/4/27

N2 - The thermal rearrangement of several N-nitrosoamides was studied by 1H NMR in the context of reversible encapsulation. The N-nitrosoamide guests were isolated from the bulk solvent in a hydrogen-bonded dimeric host capsule which prevented their rearrangement. The guests appear to be preserved in their ground state conformations by the pressure exerted by the host. The conformations of the free and bound N-nitrosoamides are of comparable relative energies as determined by DFT calculations.

AB - The thermal rearrangement of several N-nitrosoamides was studied by 1H NMR in the context of reversible encapsulation. The N-nitrosoamide guests were isolated from the bulk solvent in a hydrogen-bonded dimeric host capsule which prevented their rearrangement. The guests appear to be preserved in their ground state conformations by the pressure exerted by the host. The conformations of the free and bound N-nitrosoamides are of comparable relative energies as determined by DFT calculations.

KW - Hydrogen bonding

KW - N-Nitrosoamides

KW - Reversible encapsulation

UR - http://www.scopus.com/inward/record.url?scp=79953176263&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.11.030

DO - 10.1016/j.tetlet.2010.11.030

M3 - Article

AN - SCOPUS:79953176263

SN - 0040-4039

VL - 52

SP - 2100

EP - 2103

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Reactivity of N-nitrosoamides in confined spaces

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this