Talk:Silanol

Organosilicon category

From what I understand silanol does not belong in the Category:Organosilicon compounds, right?--Kupirijo 06:58, 8 November 2007 (UTC)[reply]

Category:Inorganic silicon compounds ??? Sorry, the bond Si-H clearly deals with organo-silicon compounds ! The silanol compound does not exist in nature and is only synthesized by organic chemists (silicone, siloxane, ... chemistry).

The frontiers between organic and inorganic chemistry are sometimes fuzzy, but some common sense should always prevail. No inorganic chemist or mineral chemist shall recognise silanol as an inorganic compound. If for some chemists a C-H bond is an indicative feature for organic compounds, the same definition could also be applied to silicon compounds: a Si-H bond is also a characteristic feature for organo-silicon compounds. Shinkolobwe (talk) 14:29, 29 January 2011 (UTC)[reply]

I imagine many chemists consider a C-H bond an essential feature of an organic compound, making such carbon compounds as CF₄ inorganic.

I don't have a strong opinion on the matter, because I think trying to draw a line between inorganic and organic compounds is unnecessary and arbitrary.

I would, however, consider a C-Si bond necessary for a compound to be organosilicon. A C-Si bond is not in itself sufficient for a compound to be organosilicon, however: SiC is inorganic.

Likewise, I think the presence of an Si-H bond is neither necessary nor sufficient to categorise a compound as organosilicon. I consider SiH₄ inorganic, as metal and metalloid hydrides are usually considered inorganic (think germane, borane, aluminium hydride, digallane, arsine, hydrogen telluride). Conversely, trimethylsilyl compounds like tetramethylsilane, trimethylsilyl chloride and so on are definitely organosilicons, despite lacking an Si-H bond.

I don't think there's much of a chemical or physical reason to define the border between inorganic and organic compounds in any particular way, so that just leaves convention. I feel our categorisation should reflect the conventions mainstream chemistry adopts, rather than letting our personal opinions on the matter choose. That way, there's much less chance of us having to recategorise things in future — if anyone challenges our categorisation on chemical or physical grounds, we simply state that such grounds are not the criterion we use, whereas convention in the literature and textbooks is.

How does the literature generally categorise silanol? Let's find out.

Ben (talk) 18:14, 29 January 2011 (UTC)[reply]

Thank you for your answer and your wize suggestion: it is a logical approach and it is perfect for me too. Sorry to have been bold (WP:BB) here, but I am happy of the answer it triggered. I aggree with you that is makes absolutely no sense to draw an arbitrary boundary between organic and inorganic chemistry. However, these last times some of my recent edits were reverted on arbitrary bases, by an editor argueing the lack of C-H bond in a compound to label it as inorganic, ... and I just followed your reasoning. Cheers, Shinkolobwe (talk) 23:33, 29 January 2011 (UTC)[reply]

It's good to be bold, please don't interpret my comments as an attack on your categorisation of silanol as organosilicon. I think it's a grey area, I'm more interested in avoiding drawn out disputes. I think we need to agree a simple policy and write it down at Wikipedia:Manual of Style (chemistry), so we can all be confident in our categorisation efforts.

I'll continue the discussion at Wikipedia talk:WikiProject Chemicals#Inorganic vs. Organic.

Ben (talk) 01:39, 30 January 2011 (UTC)[reply]

Recommend move to functional group

I suggest that this article would be far more useful to readers if it focused on the silanol functional group. According to a search of "silanol" in Chemical Abstracts (reviews only, 1980-), all the main hits are to silanols in chromatography or surface science. According to a major review (Advances in Inorganic Chemistry Volume 42, 1995, Pages 147–262 "The Synthesis and Structure of Organosilanols" Paul D. Lickiss), the compounds SiH_4-x(OH)_x are "far too unstable towards condensation reactions to be isolated and structurally characterized" We all appreciate articles on theoretically interesting species, but in this case, the great majority of readers are probably not seeking insights into H₃Si(OH), but into the functional group. In the proposed revision, we could have a section on the parent silanols SiH_4-x(OH)_x, giving their CAS#. Suggestions and critiques welcome!--Smokefoot (talk) 15:26, 30 December 2012 (UTC)[reply]

I agree with Smokefoot and support this change, someone searching for "silanol" is much more likely looking for silanol functional groups than for specifically H₃SiOH. So long as the compound is mentioned (and it is), devoting most of the article to the FG is eminently sensible. Thanks for making the change. EdChem (talk) 15:12, 12 January 2013 (UTC)[reply]

Should we add the Gold Book definitions somewhere? --Leyo 00:26, 17 April 2013 (UTC)[reply]

Triethylsilanol

The article currently includes the following: "For Et₃SiOH, the pK_a is estimated at 13.6 vs. 19 for tert-butyl alcohol." This sentence is offered in support of the assertion that silanols are generally more acidic than their related alcohols. The problem is that the silanol related to tert-butanol is trimethylsilanol and not triethylsilanol. I suggest either the pK_a for 3-ethyl-3-pentanol (Et₃COH) be provided instead of that for tert-butanol or the silanol be changed to trimethylsilanol, so that a direct comparison is not complicated by differences in the carbon skeleton. Thoughts? EdChem (talk) 15:09, 12 January 2013 (UTC)[reply]