Wikipedia:Articles for deletion/Binary ethylenimine


 * The following discussion is an archived debate of the proposed deletion of the article below. Please do not modify it. Subsequent comments should be made on the appropriate discussion page (such as the article's talk page or in a deletion review).  No further edits should be made to this page.

The result was keep. This closure still leaves open the possibility of an article merge if the page editors decide this is needed or useful.  Spinning Spark  17:43, 16 November 2012 (UTC)

Binary ethylenimine

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"Dimeric aziridine" does not exist. The reference does not claim it creates dimeric aziridine, it merely generates aziridine in situ, instead of using pre-prepared aziridine. Therefore, this lemma covers a non-existent thing and it cites a source that does not claim to create this thing. Stijndon (talk) 22:00, 8 November 2012 (UTC)


 * Keep or possibly merge It seems that the whole nomination pivots around a simple small content issue -the "dimeric aziridine" problem. But first of all: notability. That binary ethylenimine 1)exists and 2)is notable is obvious from the huge amount of academic literature (see also PubMed). If the content of the article is inaccurate, we can solve by editing and improving, not deletion, so the keep vs. delete debate is covered.


 * What about the keep vs merge possibility? Binary ethylenimine is actually a preparation of aziridine/ethyleneimine as explained here: The inactivant was called binary ethyleneimine or BEI because it is prepared from two substances, 2-bromoethylamine HBr (BEA) and NaOH, and also to distinguish this preparation from pure EI". So far, it seems it's just a synonym of ethyleneimine/aziridine. But it is actually discussed separately in the paper. Inside this paper it refers to binary ethylenimine as explicitly different: EI (ethyleneimine) is a very stable and inexpensive reagent, but like other EI derivatives (4) and beta-propiolactone, it requires very careful handling. [...] In contrast, BEI (binary ethyleneimine) has the advantages of having the same stability and low price as EI, and of being less hazardous to handle. (p. 121-122). This patent seems possibly to imply that it is considered a separate form of aziridine: The preferred aziridine compound is binary ethyleneimine (BEI). Other examples are trimeric ethyleneimine (TEI) and acetyl-ethyleneimine. Here too aziridine and binary ethyleneimine are considered separately. "Ethylenimine dimer" is listed seldomly in the literature too, with at least one reference claiming it is a virus inactivator, like BEI -this is possibly what swayed the article author. My impression from the literature is that the way of preparation creates a mixture or complex that stabilizes the aziridine, helping in handling and use for virus inactivation -and given that most sources consider BEI as something separated and different from pure aziridine, I guess we should follow their lead. But there are also good arguments for a merge. However, deletion doesn't look like a sensible option here. -- Cycl o pia talk  22:43, 8 November 2012 (UTC)
 * I now removed the "dimeric aziridine" mention from the article . -- Cycl o pia talk  22:47, 8 November 2012 (UTC)


 * Keep, largely as above. There's a huge volume of literature on this topic, include material in Vaccine and the Journal of Clinical Microbiology, plus a ton more in veterinary science journals.  Would that all the medical chemistry topics that come to AFD had that sourcing available.  Accordingly, I'm pretty sure we should follow the lead of the field and not merge this anywhere.  I'm also dubious about whether this is a unique compound or just a unique mixture of compounds, but as far as inclusion is concerned, that's a distinction without a difference.  Cleanup would be good though; a read-through the of the extensive literature, better sourcing, and clearer article wording would be laudable goals here. Squeamish Ossifrage (talk) 22:56, 8 November 2012 (UTC)


 * Delete and redirect to aziridine I am the one who nominated it for deletion in the first place, and I'll explain my motives more clearly here: binary ethylenimine is not a thing. It is actually just bromoethylamine being used to achieve the same effects that aziridine would achieve. What this effect is, is the alkylation of free amines, thiols, and possibly alcohols in proteins (or possibly nucleic acids) through their nucleophilic attack on either the formed aziridine, or on the bromine-bearing carbon of bromoethylamine. But since aziridine rapidly forms in situ, because the intramolecular reaction is faster than any intermolecular one, it behaves the same as regular aziridine would. The fact that biologists or clinicians in the past have called it binary ethylenimine (maybe because it requires two steps?) or the completely wrong dimeric aziridine does not mean that that makes sense. In general, I am an inclusionist, but this article just makes no sense. I guess it would be the best solution for all to empty this page, make it a redirect to aziridine, and then create a chapter in the aziridine page called "binary ethylenimine" where we explain that in some cases, an in situ generation is used over addition of the pre-prepared compound. That chapter could then contain the scraps of info that can be scavenged from this article. If we choose this option, then people looking for the term "binary ethylenimine" will still find information about it, but also there will be one less undeserving article.
 * Of course binary ethylenimine is discussed separately from aziridine in papers that discuss it. You use a different method, so you need to separately discuss it. In theory, if you would use the same compound but from different vendors, you would already need to separately discuss it. The thing is that it's the same chemistry that they're performing. The fact that scientific rigour requires separate discussion does not mean that there should be different articles on each strategy. It al boils down to "we alkylate the nucleophiles, yay." If this would be deserving of a separate article, then all methods where they vary the base or any of the concentrations would deserve that, too.
 * A reason people prefer this two-step protocol would be that with bromoethylamine, you can make the amine a salt during storage to make it involatile. If it's not a gas, it's less dangerous because you'll no longer accidentally breathe it in. You then turn it into the volatile (and thus 'dangerous') aziridine only when you need it. Therefor, another option is to create a page for bromoethylamine (which is the compound that's actually "binary ethylenimine") and redirect this to that. But since binary ethylenimine is just a method for using aziridine, I still believe the above option is best: deleting this page and scavenging some info for an addition to aziridine. Stijndon (talk) 08:38, 9 November 2012 (UTC)
 * Apart from the minor form issue that you are not expected to !vote after nominating, I welcome your insightful explanation. First of all, you are actually proposing a merge, not a full deletion. Therefore instead of using first PROD and then AFD, you should have proposed a merge (or directly done it yourself). Second: All what you say (btw: sources?) seem to point in the direction of keeping the article. You say: "The fact that biologists or clinicians in the past have called it binary ethylenimine (maybe because it requires two steps?) or the completely wrong dimeric aziridine does not mean that that makes sense." - But we're not here to make a scientific nomenclature debate. Lots of sources discuss aziridine and BEI as two different things, for reasons that are practical and make perfect sense. You also state "You use a different method, so you need to separately discuss it." - And this method is what the article (or the merged section) should be about, no more, no less. Yes, the end chemistry is the same, but that a distinct method of obtaining such chemistry is so clearly singled out and discussed in the literature makes it notable on its own. -- Cycl o pia talk  11:21, 9 November 2012 (UTC)
 * So is it okay if I merge this into aziridine? Stijndon (talk) 13:21, 9 November 2012 (UTC)
 * At this point, let's wait for the AfD to take its course before acting -we have a week to gauge consensus. -- Cycl o pia talk  14:13, 9 November 2012 (UTC)


 * Keep Seems Stijndon is using a lot of information to show the topic is notable, if controversial. A merge might be okay, but there appears to be a lot of information, enough for keeping it. -Fjozk (talk) 01:02, 10 November 2012 (UTC)
 * Note: This debate has been included in the list of Medicine-related deletion discussions. • Gene93k (talk) 15:06, 9 November 2012 (UTC)
 * Note: This debate has been included in the list of Science-related deletion discussions. • Gene93k (talk) 15:06, 9 November 2012 (UTC)


 * Merge given Cycl o pia  comments and Stijndon's explanation. --Bejnar (talk) 11:22, 15 November 2012 (UTC)
 * Merge. This is in essence a use of aziridine, even though it is chemically a bit more complicated than that (a poorly-defined mixture of chemical compounds that consists mainly of aziridine, but also contains related chemicals that perform the same function as aziridine).  It makes most sense to discuss this at aziridine in the context of a biochemical use of aziridine.-- Ed (Edgar181) 16:19, 15 November 2012 (UTC)
 * The above discussion is preserved as an archive of the debate. Please do not modify it. Subsequent comments should be made on the appropriate discussion page (such as the article's talk page or in a deletion review). No further edits should be made to this page.