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Structural abbreviations

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There is an excellent introduction to the use of abbreviations in general at http://www.chem.qmul.ac.uk/iupac/misc/symbols.html. We probably want to steal some of it.

Other lists of abbreviations: http://www.chem.qmul.ac.uk/iupac/AminoAcid/A1819.html, http://www.27eps.unina.it/manuscripts3.htm, http://themerckindex.cambridgesoft.com/TheMerckIndex/AdditionalTables/pdfs/AbbreviationsandSelectedDefinitions.pdf, http://scooter.cyto.purdue.edu/pucl_cd/flow/vol4/4_teach/data/acronyms/acron.htm, http://www.chem.ucalgary.ca/courses/551/listofabbreviations.pdf, http://www.users.totalise.co.uk/~tbroom/acrobat/chem.pdf, http://www.galchimia.com/downloads/files/200Problems.pdf, https://paragon.acs.org/paragon/ShowDocServlet?contentId=paragon/menu_content/authorchecklist/jo_authguide.pdf

 

The following nicknames (with capitalization as shown) may be used without further explanation to refer to the structures shown. In all cases, the nicknames should be used to refer only to the specific structures shown, without further substitution and without the presence of further charges, radicals, or non-natural isotopy.

Authors are welcome to create their own abbreviations as well, but any abbreviations not included in the list below should be defined clearly when they are used. When creating new abbreviations, it is recommended that an all-caps style be used for abbreviations that are formed as acronyms (BOM = Benzyl Oxy Methyl), while an initial-caps style should be used for abbreviations that are formed simply by shortening a longer word (Ac = Acetyl).

Several of the abbreviations listed below include portions of the text in italics. The italicization shown is the preferred formatting of those abbreviations. However, the corresponding forms without capitalization are also acceptable. [Yes? Or should we recommend only one or the other?]

The first column in the table below indicates whether it is listed at http://www.chem.qmul.ac.uk/iupac/misc/symbols.html. The second column indicates whether we want to continue to recommend that that abbreviation can be used without further explanation..

Listed? Recommend? Abbreviation Other
Abbreviations
Full structure
yes yes Ac  
  yes? Acm  
yes ? Act  
  yes? 9-BBN  
  yes? Bn  
yes yes Boc
BOC
t-BOC
  yes? BOM  
  yes? BPOC  
  yes? Bs  
  yes? Bt  
yes yes BTM  
yes yes Bu (recommended) Bun
n-Bu
  yes? Bui i-Bu  (recommended)
iBu
  yes? Bun Bu  (recommended)
n-Bu
nBu
  yes? Bus s-Bu (recommended)
sBu
yes yes But t-Bu  (recommended)
tBu
yes yes Bz  
yes ? Bza  
yes ? Cam  
yes ? Cbm  
  yes? Cbz
CBZ
 
yes yes cHx Cy (recommended)
yes ? Cm  
  yes Cp  
yes yes cPe  
  yes Cy (recommended) cHx
  yes? Ddz  
yes yes DEAE  
yes yes DNP  
yes yes Dns  
yes yes Et  
  yes? FMOC  
  yes? i-Bu (recommended) Bui
iBu
  yes? i-Pr (recommended) iPr
Pri
  yes? iBu Bui
i-Bu (recommended)
  yes? iPr i-Pr (recommended)
Pri
yes ? Ips  
yes ? Mal  
yes yes Me  
  yes? MEM  
  yes? Mes  
  yes? MOM  
  yes? Ms  
yes ? Mtc  
  yes? MTM  
yes ? Mz  
  yes? n-Bu Bu (recommended)
Bun
nBu
  yes? n-Pr nPr
Pr (recommended)
Prn
  yes? nBu Bu (recommended)
Bun
n-Bu
  yes? nPr n-Pr
Pr (recommended)
Prn
  yes? Nb  
yes ? Nbs  
yes ? NSu  
  yes? PCP  
yes ? Pe  
yes yes Ph  
yes yes Pht  
yes ? Pip  
  yes? Piv  
  yes? PMB  
yes yes POC  
yes yes Pr n-Pr
nPr (recommended)
Prn
  yes? Pri i-Pr (recommended)
i
Pr
  yes? Prn n-Pr
nPr
Pr (recommended)
yes ? Ptc  
yes ? Pz  
yes ? Qu  
  yes? s-Bu (recommended) Bus
sBu
  yes? sBu Bus
s-Bu (recommended)
yes ? Suc  
  yes? t-BOC BOC (recommended)
Boc
  yes? t-Bu (recommended) But
tBu
  yes? tBu But
t-Bu (recommended)
  yes? TBDMS (recommended) TBS
  yes? TBDPS  
  yes? TBS TBDMS (recommended)
  yes? TES  
  yes? Tf  
  yes? THP  
  yes? TIPS  
  yes? TMS  
yes yes Tos Ts (recommended)
  yes? Tr Trt (recommended)
  yes? TROC  
yes yes Trt (recommended) Tr
  yes? Ts (recommended) Tos
         
         

 

 

The following abbreviations have been used in some circumstances, but it is proposed that they no longer be recommended:

Listed? Recommend? Abbreviation Other
Abbreviations
Full structure Comments
yes? no? Z Cbz
CBZ
Andrey: I'd say No for "Z" (Cbz) seems better as soon as Z has some meaning of variable group, as X, Y, Z...

Jonathan: I've also seen it used in circumstances where it can be confused with a stereochemical indicator

SUGGESTED:

The use of the abbreviation "Z", for benzoxycarbonyl-, is not recommended. If an abbreviation for that structure is desired, "CBZ" should be used instead. [Note: this is a departure from the recommendations at http://www.chem.qmul.ac.uk/iupac/misc/symbols.html.]

yes no? Bzl Bn Andrey: not sure that it is used often and close to Bz -- benzoyl

SUGGESTED:

The use of the abbreviation "Bzl", for benzyl-, is not recommended, in large part because of its easy confusion with "Bz" for benzoyl-. If an abbreviation for that structure is desired, "Bn" should be used instead. [Note: this is a departure from the recommendations at http://www.chem.qmul.ac.uk/iupac/misc/symbols.html.]

 

yes no? Np   Andrey: I vote by two hands against Np and Nps/NpS/SNp. The reason is that even for IUPAC page there are:
-SNp          for 4-nitrophenylthio and
NpS-/Nps- for 2-nitrophenylthio
If it is not a misprint, it is very bad that simple changes of direction lead to different structures.

(Also in general case, abbreviation that imply but doesn't cite exact position of substitutent could be less preferred if we need reason for our decision about some of them.)

yes no? Nps  

(see previous)

yes no? Snp   (see previous)
yes yno? Bzh   Andrey: Not sure about Bzh (benzhydryl) - quite rare and may be simply drawn with common Ph labels.

Jonathan: Yup: only five pages on google have "Bzh" and "benzhydryl"

  yes? TCP   Andrey:
  1. TCP in chemistry is most often used for substances and most often for 2,4,5-trichlorophenol an dless for tricresyl phosphate (also found for 2,3,5,6-tetrachloropyridine) (even most hits with both "TCP" and "trichlorophenyl" mention TCP only for 2,4,5-trichlorophenol)
  2. this abbreviation itself doesn't state the positions of chloro in phenyl
  3. "T" can be used both for tri and tetra
  4. Not sure that it is often used.

Keith: In the Auk,TCP is also an OTC antiseptic. Yes, the active ingredient is trichlorophenol. So best avoided.

Should we list amino acids here or just reference the amino acids doc?
Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, Val (see longer list at
http://www.chem.qmul.ac.uk/iupac/misc/symbols.html)

How about inorganic ligands (cross-ref to the revised Red Book)?

Note: ChemDraw also has the following nicknames predefined. Should any of them be included in the list above?
Ad, Alloc, Am, Bt, BzOM, c-C3H5, c-C4H7, c-C5H9, c-C6H11, c-C7H13, c-C8H15, c-Hx, CoA, Cy, Dan, DEIPS, DMIPS, DMPM, DMPS, DMTr, DNS, DPIPS, DPTBS, DTBMS, DTBS, i-Am, Im, MDIPS, MDPS, MMTr, MPM, n-Am, neo-Am, PMBM, PNB, PPi, Pv, s-Am, SEM, SES, t-Am, TBMPS, TDS, TFA, THF, TIPDS, Xyl

What about ISIS/Draw, ChemSketch, etc?