A Nuclear Magnetic Resonance Study of the 2-Haloethylamines

Levins, P.L.; Papanastassiou, Zinon B.

doi:10.1021/ja01082a023

Cited by 41 publications

(13 citation statements)

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“…Such samples, which remained homogeneous at 20 °C following heating at 37 °C (15 h), afforded a complex spectrum that was not interpretable with regard to product identification, except for a low-field doubled triplet indicative of CH2CH2OP (3Jhh = 6 Hz, 3Jhp = 14 Hz) and a high-field AA'XX' aziridinyl ring proton pattern. 21 It was also found that basification (pH ~14) of control solutions of either 3-DC1 (0.1 M) or 3-aminopropanol and nor-HN2-HCl (1:1,0.1 M) did not produce spectra which simulated the alkaline reaction mixture derived from 1; however, the liberated nor-HN2 did lead to aziridinyl proton absorptions. These observations militate against the intermediacy of 3 and indicate that the chloride ion formation reported earlier8 for 1 under basic conditions results from facile21 2chloroethylamino group cyclization.…”

Section: Resultsmentioning

confidence: 96%

High-resolution nuclear magnetic resonance investigations of the chemical stability of cyclophosphamide and related phosphoramidic compounds

Zon¹,

Ludeman²,

Egan³

1977

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 96%

High-resolution nuclear magnetic resonance investigations of the chemical stability of cyclophosphamide and related phosphoramidic compounds

Zon¹,

Ludeman²,

Egan³

1977

J. Am. Chem. Soc.

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“…During the latter half of the 20th century, however, NMR emerged as a powerful tool, especially for solution studies, and thus has been used to explore the detailed reaction pathways of the chemical mustards. 72,73 One of the key studies in this regard was that of Golding and co-workers. 74 In 1987 the Golding group studied the reactions of the nitrogen mustard HN2 with various nucleophiles in aqueous buffered solution using 1 H and 13 C NMR.…”

Section: Reactivity Of Nitrogen Mustardsmentioning

confidence: 99%

Sulfur, oxygen, and nitrogen mustards: stability and reactivity

et al. 2012

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Mustard gas, bis(β-chloroethyl) sulfide (HD), is highly toxic and harmful to humans and the environment. It comprises one class of chemical warfare agents (CWAs) that was used in both World Wars I and II. The three basic analogues or surrogates are: the monochloro derivative, known as the half mustard, 2-chloroethyl ethyl sulfide (CEES); an oxygen analogue, bis(β-chloroethyl) ether (BCEE); and several nitrogen analogues based on the 2,2'-dichlorodiethylamine framework (e.g., HN1, HN2, and HN3). The origin of their toxicity is considered to be from the formation of three-membered heterocyclic ions, a reaction that is especially accelerated in aqueous solution. The reaction of these cyclic ion intermediates with a number of important biological species such as DNA, RNA and proteins causes cell toxicity and is responsible for the deleterious effects of the mustards. While a number of studies have been performed over the last century to determine the chemistry of these compounds, early studies suffered from a lack of more sophisticated NMR and X-ray techniques. It is now well-established that the sulfur and nitrogen mustards are highly reactive in water, while the oxygen analog is much more stable. In this study, we review and summarize results from previous studies, and add results of our own studies of the reactivity of these mustards toward various nonaqueous solvents and nucleophiles. In this manner a more comprehensive evaluation of the stability and reactivity of these related mustard compounds is achieved.

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“…In a mosaic unsuitable for the species under study, the functional significance of corridors and the related concept of connectivity have been investigated mostly for animal species (Andreassen et al 1998, Mö nkkö nen andReunanen 1999). Island biogeography theory (MacArthur and Wilson 1967), metapopulation theory (Levins 1970, Levin 1976, Hanski 1983, source-sink model (Pulliam 1988), percolation theory (Johnson et al 1992), or the focal species approach (Lambeck 1997) have provided theoretical foundation and guidelines leading to some level of conceptual integration of animal ecological studies at the landscape scale. Recent developments seem to have significantly improved the ability to predict complex patterns of species presence and abundance for a wide variety of vertebrate and invertebrate taxa and landscape type (reviewed in Mazerolle and Villard 1999).…”

mentioning

confidence: 99%

Landscape issues in plant ecology

Blois¹,

Domon²,

Bouchard³

2002

Ecography

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In the last decade, we have seen the emergence and consolidation of a conceptual framework that recognizes the landscape as an ecological unit of interest. Plant ecologists have long emphasized landscape‐scale issues, but there has been no recent attempt to define how landscape concepts are now integrated in vegetation studies. To help define common research paradigms in both landscape and plant ecology, we discuss issues related to three main landscape concepts in vegetation researches, reviewing theoretical influences and emphasizing recent developments. We first focus on environmental relationships, documenting how vegetation patterns emerge from the influence of local abiotic conditions. The landscape is the physical environment. Disturbances are then considered, with a particular attention to human‐driven processes that often overrule natural dynamics. The landscape is a dynamic space. As environmental and historical processes generate heterogeneous patterns, we finally move on to stress current evidence relating spatial structure and vegetation dynamics. This relates to the concept of a landscape as a patch‐corridor‐matrix mosaic. Future challenges involve: 1) the capacity to evaluate the relative importance of multiple controlling processes at broad spatial scale; 2) better assessment of the real importance of the spatial configuration of landscape elements for plant species and finally; 3) the integration of natural and cultural processes and the recognition of their interdependence in relation to vegetation management issues in human landscapes.

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A Nuclear Magnetic Resonance Study of the 2-Haloethylamines

Cited by 41 publications

References 1 publication

High-resolution nuclear magnetic resonance investigations of the chemical stability of cyclophosphamide and related phosphoramidic compounds

High-resolution nuclear magnetic resonance investigations of the chemical stability of cyclophosphamide and related phosphoramidic compounds

Sulfur, oxygen, and nitrogen mustards: stability and reactivity

Landscape issues in plant ecology

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