Talk:Thionyl chloride

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Preparation[edit]

Does anyone know easier steps to get the synthesis of Thionyl chloride??

I recall making SOCl2 in high school via one of the methods you show, SO2 and PCl5, it is easy. Greenwood & Earnshaw (Chemistry of the Elements) indicates that this is the standard lab method, but on an industrial scale it is done via SO3 + SCl2 → SOCl2 + SO2. The third method shown presently is in effect a sum of the second method + this industrial route. I will add the industrial process to the page. Walkerma 15:58, 6 Apr 2005 (UTC)

we are getting the coloured(reddish/marun colour)impurities during manufacturing of thionyl chloride. what is the reason for this? if any one can find then send me at following email address : alpesh20002001@yahoo.co.in thanks

Links[edit]

Does anyone know why thionyl bromide is listed as an anion under related compounds?Haligonian1 14:14, 14 June 2007 (UTC)[reply]

It uses a standard chembox for inorganic compounds, and most of these were salts. I've changed "anions" for "halogens" which is the appropriate term here. Thanks for pointing it out! Walkerma 14:42, 14 June 2007 (UTC)[reply]

Graphics[edit]

I think the new grahics have phosgene instead of thionyl chloride as a reagent, maybe this could be changed. I'm with gerrit (talk) 21:34, 21 January 2008 (UTC)[reply]

you are quick! (replacement pics underway...) V8rik (talk) 21:40, 21 January 2008 (UTC)[reply]
done V8rik (talk) 21:44, 21 January 2008 (UTC)[reply]

Not sure if this is where I post this but the mechanism posted for acetyl chloride synthesis is incorrect, someone fix it I don't have time.

Structure of Thionyl Chloride[edit]

The structure that is shown is incorrect. In particular, the S-Cl are way too short. I have performed a variety of quantum mechanical calculations of this molecule and in all cases the S-Cl bond is around 200 pm. That is quite comparable to the sum of the covalent radii of the two atoms. I have built a Jmol page showing the structure and the bond lengths and angles from a DFT/B3LYP calculation using the 6311_G(d) basis set. It is at [1]. Wfcoleman (talk) 18:33, 18 February 2009 (UTC)[reply]

~~Got a peer-reviewed reference for this?~~

Experimental data is obvious preferred to calculations, but you make a valid point. The CRC Handbook gives d(S=O) = 1.44 Å, d(S-Cl) = 2.072 Å, ∠Cl-S-Cl = 97.2°, ∠O=S-Cl 108.0° (from microwave spectroscopy). I'll try and find an original paper.

I really don't know where I got the dimensions from when I made File:Thionyl-chloride-2D-dimensions.png, but it must have been a mistake. I'll make a replacement image ASAP.

Thanks very much for noting this error.

Ben (talk) 19:09, 18 February 2009 (UTC)[reply]

Here we go: J. Mol. Struct. (1983) 101 233-238. MW data: (S=O) = (1.4278±0.0005) Å, d(S-Cl) = (2.0744±0.0003) Å, ∠Cl-S-Cl = (96.9547±0.0013)°, ∠O=S-Cl (107.958±0.022)°.

New image on the way.

Ben (talk) 19:23, 18 February 2009 (UTC)[reply]

The dimensions given in the incorrect image are in fact the dimensions of thionyl fluoride, SOF₂, from R.C. Ferguson, J. Am. Chem. Soc. (1954) 76, 850-853. I must have accidentally used these values when I made the image in January 2007. Sorry about that.

I have now updated the image with dimensions from gas-phase microwave spectroscopy and single crystal X-ray crystallography. There are two further images, showing the more precise values determined by each of these two techniques:


from MW	from XRD

Ben (talk) 18:19, 22 February 2009 (UTC)[reply]

Assessment comment[edit]

The comment(s) below were originally left at Talk:Thionyl chloride/Comments, and are posted here for posterity. Following several discussions in past years, these subpages are now deprecated. The comments may be irrelevant or outdated; if so, please feel free to remove this section.

The structure shown for thionyl chloride is incorrect. In particular the S-Cl bonds are much shorter than they should be. My calculations at the DFT/B3LYP level using the 6311-G(d) basis set show the bond lengths to be about 200 pm. The bond length is similar in a variety of Hartree-Fock and DFT methods, and is consistent with the sum of the covalent radii of the two atoms. The structure is shown at [2]. Wfcoleman (talk) 17:50, 18 February 2009 (UTC)[reply]

Last edited at 17:50, 18 February 2009 (UTC). Substituted at 08:34, 30 April 2016 (UTC)

Orphaned references in Thionyl chloride[edit]

I check pages listed in Category:Pages with incorrect ref formatting to try to fix reference errors. One of the things I do is look for content for orphaned references in wikilinked articles. I have found content for some of Thionyl chloride's orphans, the problem is that I found more than one version. I can't determine which (if any) is correct for this article, so I am asking for a sentient editor to look it over and copy the correct ref content into this article.

Reference named "clayden":

From Acyl chloride: Clayden, Jonathan (2001). Organic chemistry. Oxford: Oxford University Press. pp. 276–296. ISBN 0-19-850346-6.
From Dimethylformamide: Clayden, J. (2001). Organic Chemistry. Oxford: Oxford University Press. pp. 276–296. ISBN 0-19-850346-6.

I apologize if any of the above are effectively identical; I am just a simple computer program, so I can't determine whether minor differences are significant or not. AnomieBOT ⚡ 18:25, 7 August 2020 (UTC)[reply]

In pop culture[edit]

It plays a role in the movie Ruby Cairo. Is this at all worth mentioning in the article? Kdammers (talk) 19:10, 11 June 2023 (UTC)[reply]