User:Smokefoot

About me

I mainly edit pages describing chemical compounds, especially inorganic, organometallic, and organic species. My favorites contain sulfur. I am a highly imperfect copy editor, so I am not bothered by having my English polished and especially welcome having my chemistry corrected.

My continuing focus remains on industrially significant compounds and boring topics like laundry detergents and waxes and related goopy stuff. Such themes are often overlooked since most editors are more familiar with academic topics, whereas our society and environment are more strongly influenced by the industrial-scale applications, for better or worse. Much of my content comes from Ullmann's Encyclopedia of Industrial Chemistry, which appears to be authoritative and objective. Another interest is specialty reagents, with an eye toward increasing the value of Wikipedia for the synthetic chemist.

I am professionally associated with technical journals and book series, many of which are cited in my editing, but these relationships result in no financial rewards (unfortunately) to me. If editors have concerns that my edits "cross the line," please say so. Only rarely have I cited my own work or work by colleagues and friends.

Comment on refs

To select references on a mature topic, one almost needs to go with books or their electronic equivalent. Even reviews are often tainted with hype. Particularly good sources are Kirk-Othmer Encyclopedia of Chemical Technology and Ullmann's Encyclopedia of Industrial Chemistry. One can pick a big topic (like automotive fuels, which I have been playing with lately) and check it against our Wiki article. You might find all sorts of mistakes and especially WP:UNDUE. Fact checking big topics often does not require advanced chemical knowledge. The catch is that you got to get your hands on a pdf of a chapter in Kirk-Othmer or Ullmann's. To do that, you need electronic access to a university library directly or through a colleague/friend. So if you are determined to edit, your first mission should be to get the pdf.

Here are the themes in Kirk-Othmer (number of articles in parentheses): Agrochemicals (14), Analytical Techniques (39), Biochemistry & Biotechnology (38), Chemical Reactions (37), Dyes and Pigments (41), Energy (57), Environmental Protection, Industrial Safety (56), Fat, Oil, Food and Feed, Cosmetics (73), Inorganic Chemicals (181), Materials (113), Metals and Alloys (37), Organic Chemicals (174), Pharmaceuticals (101), Polymers and Plastics (119), Processes & Process Engineering (165), Renewable Resources (24), Special Topics (135)

Teaching chemistry through Wikipedia

Thinking about using Wikipedia as part of your chemistry course? Doing so gives students experience integrating chemical knowledge and in copy-editing, both relevant to their professional development. In terms of implementation, here are my observations based on several years of experience.

• The most important step is the selection of topics that allow students to contribute new content. The instructor should make sure that good general sources exist on the assigned topics, preferably reviews and textbooks. A major part of the learning experience comes from students re-describing or summarizing what they read from these broad sources.
• Learning Wikipedia techniques is almost irrelevant to the educating students. To this end, it can be useful for the instructor to set up new articles with examples of linking and reference format. Students can then readily add to this article, even without registering as a user.
• Students should be graded on the quality of their content, not the quantity.
• Peer review (by fellow students) is a joke, how can a fellow student critique an article on topics that they barely fathom, not to mention dealing with conflict of interest in grading their friends?
• Steer away from toxicity, environmental, or safety aspects. Tons of content on such topics are readily Google-able. Students learn little from parroting this material and can be poor judges of quality sources. Teach them chemistry - mechanisms, (bio)synthesis, structure, bonding, spectroscopy, reactivity, ... Help them sort notable from non-notable aspects.
• Bear in mind that editors at Wikipedia are not supposed to serve babysitters or graders for your class. Instructors need to be involved, but they could expect good cooperation from established editors.

WP:SECONDARY for technical editing: three reasons to follow this guideline

For technical articles, an important editing guideline is WP:SECONDARY. All editors cite primary sources, but conscientious editors rely more heavily on general sources. Why? Three reasons. 1) Unless you are a real expert on the area you are editing, it is presumptuous to cite primary reference. Why that one paper in lieu of hundreds or thousands of others? Citing primary references risks violating WP:UNDUE, i.e. overemphasis on a narrow result that distorts the big picture and WP:RECENTISM ('I don't know the background, but I found this nifty article today ...'). 2) Second, Wikipedia recommends reliance on secondary sources, because Wikipedia is a bloody encyclopedia - we are not a journal! Start your own blog. 3) Excessive reliance on primary sources is uncool. Primary citations are often the hallmark of vanity editors (ya gotta read my paper), kids (don't know any better), and wanna-be scholars, who think that citing primary citations establishes their credentials as players, when it does the opposite. The goal of referencing is to help readers, not the editor, by guiding reader to digested sources of information that offer broad perspective.

Again most technical editors in Wikipedia are inexpert in the topics we edit. We demonstrate our good taste by selecting broad sources.

WP:COI (Conflict of Interest): Avoid citing yourself, your family, your friends, and your colleagues

Many (or most!) new or infrequent editors come to the Chemistry part of Wikipedia not to help the readership, but to cite papers by themselves, their family, or their friends. Such citations can show bad taste and potentially present a conflict of interest. Wikipedia is not the way to establish a scientific reputation - do that the old fashioned way - publish great papers in real refereed journals! If you want to help people understand chemistry and its role in our world, then Wikipedia is the place for you.

Useful links

What readers are reading

• http://toolserver.org/%7Ealexz/pop/view.php, This tool shows the relative hit rate and quality rating of popular pages. A guide to what needs to be done.
• http://stats.grok.se/en/201203/ This tool shows the hit rate for any article.

Templates, etc that I use

• C. Elschenbroich (2006). Organometallics. VCH. ISBN 978-3-527-29390-2.
• Atkins, Peter (1994). Physical Chemistry, 5th Edition. Freeman. ISBN 7167-2402-2. {{cite book}}: Check |isbn= value: length (help)
• Silverstein, Robert M.; Webster, Francis X.; Kiemle, David J.; Bryce, David L. (2016). Spectrometric Identification of Organic Compounds, 8th Edition. Wiley. ISBN 978-0-470-61637-6.

See http://en.wikipedia.org/wiki/Category:Chemistry_citation_templates

• {{Holleman&Wiberg}} gives Holleman, Arnold Frederik; Wiberg, Egon (2001), Wiberg, Nils (ed.), Inorganic Chemistry, translated by Eagleson, Mary; Brewer, William, San Diego/Berlin: Academic Press/De Gruyter, ISBN 0-12-352651-5
• {{RubberBible87th}} gives Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3.
• {{Greenwood&Earnshaw2nd}} gives Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
• {{March6th}} gives Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
• {{Lehninger4th}} gives Nelson, David L.; Cox, Michael M. (2005). Principles of Biochemistry (4th ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.
• {{Ullmann's}} gives Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.
• {{OrgSynth|author=Whitmore, F. C.|author2=Hanson, E. R.|year=1925|title=o-Chloromercuriphenol|volume=4|pages=13|collvol=1|collvolpages=161|prep=CV1P0161}} gives Whitmore, F. C.; Hanson, E. R. (1925). "o-Chloromercuriphenol". Organic Syntheses. 4: 13; Collected Volumes, vol. 1, p. 161.

• {{cite book |doi=10.1002/0470084960|title=March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure |year=2006 |last1=Smith |first1=Michael B. |last2=March |first2=Jerry |isbn=9780470084960 }}

• Hartwig, John (2010). Organotransition Metal Chemistry: From Bonding to Catalysis. New York: University Science Books. p. 1160. ISBN 978-1-938787-15-7.

What Wikipedia is and is not, and related comments

From Wikipedia:What Wikipedia is not: "Wikipedia is an encyclopedic reference, not an instruction manual, guidebook or textbook.... a Wikipedia article should not read like a how-to style manual of instructions, advice (legal, medical, or otherwise) or suggestions..."

Citing primary literature: Wikipedia is not Chemical Reviews

Citations to the primary literature are generally not sought by Wikipedia. See WP:secondary source. Like other encyclopedias, Wikipedia seeks digested sources (reviews, monographs, texts). Chemical Abstracts Service (http://pubs.acs.org/cen/science/84/8448sci1.html; http://www.cas.org/expertise/cascontent/ataglance/index.html) abstracts many tens of thousands of papers annually. So citing the primary literature is almost impossible in a neutral manner and citing them all would ruin Wikipedia. Citations to the primary literature also invite problems with self-promotion. In the absence of more general sources, however, primary literature is a practical placeholder. I do replace primary references with broader sources, when I have the time.

Fluoride

Perhaps no element brings out stronger feelings than poor old fluorine.

Wikipedia knock-offs

• BYJUS. Maybe based on Wikipedia and then embellished. [[1]]
• Chemlibre. Slick and not bad version of Wiki-chem with educational vs encyclopedic angle. [[2]]
• Khan Academy. Focused on testing for AP credit? Limited elementary pchem focus. [[3]]

Moving option

"you might find some use in sending a request to WP:PERM#Page mover, in order to move pages without leaving behind a redirect"

fmt

{{nbsp}}

• Comment: text here

  ⇌ ${\ce {<=>>}}$ ${\ce {<<=>}}$

Small/simple form

To use, simply copy and paste the left column into the document, filling in whatever you can, or type {{subst:Chembox subst small}} and press save:

{{Chembox | ImageFile = | ImageSize = | ImageAlt = | IUPACName = | OtherNames = |Section1={{Chembox Identifiers | CASNo = | CASNo_Comment = | CASNo1 = | CASNo1_Comment = | PubChem = | SMILES = }} |Section2={{Chembox Properties | Formula = | MolarMass = | Appearance = | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

Useful reminders

{{globalize|article|the United States|date=??}} WP:SELFCITE edit comments "Attribution: content in this section was copied from xyz on June 3, 2017. Please see the history of that page for full attribution"

Frontiers Media. Junk journal.

| BoilingPt_notes = 50 mmHg  

Help:Introduction to tables with Wiki Markup/2

Template:Chem2

Use

Formula punctuation

Symbol	Gives	Example	Output
\s	−	{{chem2|CH3\sCH3}}	CH3−CH3
\d	=	{{chem2|CH2\dCH2}}	CH2=CH2
\t	≡	{{chem2|HC\tCH}}	HC≡CH
\q	≣	{{chem2|[Cl4Re\qReCl4](2−)|}}	[Cl4Re≣ReCl4]2−
\-	-
\\	\
\h	η
\h{1}	η1-
\m{1}	μ1-
->	→	{{chem2|2H2 + O2 -> 2H2O}}	2H2 + O2 → 2H2O
<->	⇌
*	·	{{chem2|CoCl2*6H2O}}	CoCl2·6H2O
\*	*	{{chem2|Cp\*2Fe}}	Cp*2Fe
_{}	subscript	{{chem2|CH4_{(g)}|}} *	CH4(g)
	another subscript	{{chem2|[Eu(H2O)_{x}](3+)}}	[Eu(H2O)x]3+
^{}	superscript	{{chem2|^{13}CH4}}</code>	13CH4
&nabla;	∇	{{chem2|&nabla;}}	∇
( )	( )	{{chem2|R\sCH(OH)CN}}	R−CH(OH)CN

^ If the last character of the template input is }, MediaWiki will confuse it with the end-of-template tag }}. Adding a space between the two resolves this ambiguity. Other options include instead inserting {{null}} or <nowiki/>.

Formulas, charges, equations

Formulas (without charge) are just written:

• {{chem2|CH3(CH2)5CH3}} → CH₃(CH₂)₅CH₃
• {{chem2|Fe3S2(CO)9}} → Fe₃S₂(CO)₉
• {{chem2|C_{''n''}H_{2''n''+2}|}} → C_nH_2n+2

Charges are written inside parentheses:

• {{chem2|SO4(2-)}} → SO2−4
• {{chem2|S19(2+)}} → S2+19

Charges +1 and −1 can be written plain:

• {{chem2|Na+}} → Na⁺
• {{chem2|O2-}} → O−2

equals {{chem2|O2(-)}}

Chemical equations:

• {{chem2|2 S + 3 O2 + 2 H2O -> 2 H2SO4}} → 2 S + 3 O₂ + 2 H₂O → 2 H₂SO₄
• {{chem2|2S + 3O2 + 2H2O -> 2H2SO4}} → 2S + 3O₂ + 2H₂O → 2H₂SO₄

The arrows can be written as -> or just →. All characters (and unicode markup) are valid input except \, = (Mediawiki use it), _ and - (endash etc.)

• {{chem2|2 H2_{(g)} + O2_{(g)} -> 2H2O_{(g)}|}} → 2 H_2(g) + O_2(g) → 2H₂O_(g)
• {{chem2|NH2RCHCO2H <-> NH3+RCHCO2-}} → NH₂RCHCO₂H ⇌ NH+3RCHCO−2

Hapticity and mu:

• {{chem2|W(CO)3(PiPr3)2(\h{2}H2)}} → W(CO)₃(PiPr₃)₂(η²-H₂)
• {{chem2|auto=yes|W(CO)3(PiPr3)2(\h{2}H2)}} → W(CO)₃(PiPr₃)₂(η²-H₂)

Red flag words, phrases, etc.

Well intentioned perhaps, but these words and phrases are usually unhelpful in this encyclopedia:

• Successful", etc ."The data were successfully recorded". Better: "The data were recorded"
• "Researchers" report that A gives B..." pretentious and semi-obvious. Better: "A gives B...[ref]"
• "Recently" (that word goes stale fast!)
• "At the University of ..." WP:BOOSTERISM
• "Different" (vs what?) "diverse" or "various"
• "Interesting", in the eyes of the beholder
• "clear solution.." thats what solutions are
• "pure compound", what other kind of "compound" is there?

Useless attention magnets

Attracting regular editing attention, many of these compounds have some or all of these characteristics: not used for anything, weakly characterized:

• Fluoroantimonic acid
• Dimanganese heptoxide
• titanic acid
• xenon hexafluoroplatinate