European Journal of Organic Chemistry

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Cover image for Vol. 2013 Issue 15

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

European Journal of Inorganic Chemistry
European Journal of Organic Chemistry


Frequently Asked Questions (and Answers)

 Q:

Why do Eur. J. Inorg. Chem., Eur. J. Org. Chem. and other Wiley-VCH journals use the term "phosphane" instead of "phosphine"?

 A:

Although the use of "phosphine" is widespread, IUPAC recommends "phosphane". The pertinent rules can be found in ref.[1-3] The main reasons for the use of "phosphane" are:

-

"The chief usefulness of the -ane names of Table I-7.2 lies in their convenience for naming substituted derivatives and their derived radical forms, as well as the ease with which the same style can be extended into the nomenclature of chains and rings." (ref.[1]: rule I-7.2.2.1, P. 85)

-

"Phosphanyl: H2P-, phosphanediyl: HP<, phosphanylidene: HP=, and phosphanetriyl: -P< are all logically derived from PH3, phosphane: Use of the name phosphine yields instead: phosphinyl, phosphinediyl, and phosphinetriyl, respectively. This conflicts with the widespread usage of 'phosphinyl' for the substituent group H2P(=O)-, which is also currently named 'phosphinoyl' by analogy with certain organic acyl groups. Therefore, names based on phosphanes are recommended as being free from this confusion." (ref.[1]: Note 7l, page 87)

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"Organic derivatives of the trivalent phosphorus, arsenic, antimony, and bismuth parent hydrides are named substitutively on the basis of parent hydride names such as phosphane, diphosphane, arsane, stibane, bismuthane, etc. (see R-2.1 and R-2.2.2). In these recommendations, the names phosphine, arsine, stibine, and bismuthine are not encouraged." (ref.[2]: R-5.1.3.2, p. 78)

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"The systematic names 'phosphane', 'arsane' and 'stibane' are used throughout this book. The names 'phosphine', 'arsine' and 'stibine' are no longer acceptable" (ref.[3]: Table IR-6.1, footnote e, page 85)

 

Thus, Eur. J. Inorg. Chem. and Eur. J. Org. Chem., together with other Wiley-VCH journals, adopted these recommendations to be used in these journals.

 

[1] IUPAC - International Union of Pure and Applied Chemistry, Nomenclature of Inorganic Chemistry - Recommendations 1990, Issued by the Commission on the Nomenclature of Inorganic Chemistry, Edited by G. J. Leigh, Blackwell Scientific Publications, Oxford, 1991 [ISBN 0-632-02319-8 or 0-632-02494-1 (pbk)].

 

[2] IUPAC - International Union of Pure and Applied Chemsitry, Organic Chemistry Division, Commission on Nomenclature of Organic Chemistry (III.1), A Guide to IUPAC Nomenclature of Organic Compounds - Recommendations 1993, Prepared for publication by R. Panico, W. H. Powell, J.-C. Richer (Senior Editor), Blackwell Science, Oxford, 1995 [ISBN 0-632-03488-2]; an online version can be found at
http://www.acdlabs.com/iupac/nomenclature/
(see especially http://www.acdlabs.com/iupac/nomenclature/93/r93_185.htm and
http://www.acdlabs.com/iupac/nomenclature/93/r93_349.htm).

 

[3] International Union of Pure and Applied Chemistry, Nomenclature of Inorganic Chemistry - IUPAC Recommendations 2005, Prepared for publication by N. G. Connelly, T. Damhus, R. M. Hartshorn, A. T. Hutton, RSC Publishing, Cambridge, 2005 [ISBN 0-85404-438-8].

 Q:

What other recent IUPAC recommendations are going to be adopted by Eur. J. Inorg. Chem., Eur. J. Org. Chem. and other Wiley-VCH journals?

 A:

According to the IUPAC Recommendations (2005) on the Nomenclature of Inorganic Chemistry[1]:

-

"Names of anionic ligands, whether inorganic or organic, are modified to end in ‘o’. In general, if the anion name ends in ‘ide’, ‘ite ’or ‘ate’, the final ‘e’ is replaced by ‘o’, giving ‘ido’, ‘ito’ and ‘ato’, respectively. In particular, alcoholates, thiolates, phenolates, carboxylates, partially dehydronated amines, phosphanes, etc. are in this category. Also, it follows that halide ligands are named fluorido, chlorido, bromido and iodido, and coordinated cyanide is named cyanido. In its complexes, except for those of molecular hydrogen, hydrogen is always treated as anionic, and therefore ‘hydrido’ is used for hydrogen coordinating to all elements including boron. Names of neutral and cationic ligands, including organic ligands, are used without modification (even if they carry the endings ‘ide’, ‘ite’ or ‘ate’)."
Examples:

 

Formula

 

Ligand name

 

PhCH2CH2Se–

 

2-phenylethane-1-selenolato

 

MeCOO–

 

acetato or ethanoato

 

Me2As–

 

dimethylarsanido

 

MeCONH2

 

acetamide (not acetamido)

 

MeCONH–

 

acetylazanido or acetylamido (not acetamido)

 

MeNH2

 

methanamine

 

MeNH–

 

methylazanido, or methylamido, or methanaminido

 

MePH2

 

methylphosphane

 

MePH–

 

methylphosphanido

 

MeOS(O)OH

 

methyl hydrogen sulfite

 

MeOS(O)O–

 

methyl sulfito, or methanolatodioxidosulfato(1–)

 

O2-

 

oxido


(ref.[1]: IR-9.2.2.3, p. 151; selected examples from pp. 151–152)

-

The term "polyoxometalate" as a generic name is allowed; however, "oxido" is the correct name to be used for the anionic ligand in the actual full names of polyoxometalates.

-

"In the formulae for coordination entities, ligands are now ordered alphabetically according to first symbol of the abbreviation or formula used for the ligand, as written, irrespective of the charge (Sections IR-4.4.3.2 and IR-9.2.3.1)."
(ref.[1]: IR-1.6.5, p. 11; IR-4.4.3.2, p. 59)

-

"Square brackets are used in formulae in the following ways.
(a) To enclose the whole coordination entity of a neutral (formal) coordination compound, for example, [Ph(O)(OH)2]. No numerical subscript should follow the square bracket used in this context. For example, where the molecular formula is double the empirical formula, this should be indicated inside the square bracket.
Example:
Sample Graphic
[{Pt(η2-C2H4)Cl(μ-Cl)}2] is more informative than [Pt2(η2-C2H4)2Cl4]; the representation [Pt(η2-C2H4)Cl2]2 is incorrect.
(b) To enclose a charged (formal) coordination entity. In this case, the superscript showing the charge appears outside the square bracket as do any subscripts indicating the number of ions in the salt.
Examples: [BH4]–, [Al(OH)(OH2)5]2+, Ca[AgF4]2"
(ref.[1]: IR-2.2.2, p. 18)

-

"Abbreviations for solvents that behave as ligands should also be in lowercase letters [e.g. dmso for dimethyl sulfoxide {(methylsulfinyl)methane}, thf for tetrahydrofuran]; the practice of capitalizing the abbreviation of a solvent when it does not behave as a ligand is strongly discouraged as an unnecessary distinction."
(ref.[1]: IR-4.4.4, p. 63)

 

[1] International Union of Pure and Applied Chemistry, Nomenclature of Inorganic Chemistry - IUPAC Recommendations 2005, prepared for publication by N. G. Connelly, T. Damhus, R. M. Hartshorn, A. T. Hutton, RSC Publishing, Cambridge, 2005 [ISBN 0-85404-438-8].

 Q:

Why are electronic proofs sent as PDF files (which need to be printed, corrected, and mailed/faxed) and not as files that can be edited (e.g. Word documents) and returned by E-mail?

 A:

The type of files generated by typesetters to prepare the proofs requires special (expensive) tools for editing and authors usually have no access to such tools. However, PDF is a widespread standard that allows us to send the author proofs by E-mail with exactly the same layout as if printed by the typesetter with a printing machine.

 Q:

Why do some special characters in the proofs look different than in the electronic file of the manuscript that was submitted or are even missing?

 A:

There are many ways to create special characters in the different current text processors. In some rare cases the conversion from other text processors into MS Word and from there into the different output file formats (SGML, HTML, PDF, and the typestter's file format) can lead to corruption or loss of information in the case of some special characters; this is a consequence of the multitude of proprietary fonts and conversion filters. Such errors should be corrected in the proofs as any other errors.

 Q:

Why is the quality of some graphics in the proofs rather low?

 A:

A lower resolution of some of the graphics keeps the file size small, which is important when sending the proofs as PDF file attachment by E-mail. The quality of the printout of a proof PDF file also depends on the printer used and its settings. The resolution of the graphics and thus the quality of the final print in the issue and of the online full texts will of course be considerably higher.

 Q:

Where can I find the Supporting Information mentioned in a particular paper?

 A:

The Supporting Information is located under http://www.eurjic.org/ or http://www.eurjoc.org/ and can be accessed by clicking on the link at the bottom of the abstract of the particular paper. The Supporting Information is in PDF format; for viewing you need Acrobat Reader which can be downloaded free from http://www.adobe.com (multi-language and multi-platform versions available).

 Q:

Why are horizontal brackets as ring indicators above linear formulae not allowed in the text?

 A:

Such horizontal brackets would be graphical elements and are therefore not allowed in the text file; they cannot be converted into HTML and therefore would be lost in the HTML full-text version on the Web. The solution is to adopt the nomenclature rules of multinuclear complexes to indicate metal-metal bonds: The element symbols to be connected are put in parentheses at the end of the corresponding part of the formula in italics with a long hyphen between them, as in for example [Fe(C5R5)(CO){C(OMe)C6H4-o-X}(Fe-X)][OTf]; if there is more than one symbol of the same kind in the formula, the one to be connected is labelled with a superscripted letter, for example [Fe(C5Me5)(CO){C(OMe)(OEt)(C6H4-o-OaMe)}(Fe-Oa)]. This way such formulae are also searchable in the full text version.

 Q:

What is the proper way of expressing NMR chemical shifts?

 A:

The The IUPAC Recommendations of 1972 defined the proton NMR shift scale in such a way that δ has no quoted units but is presumed to be in ppm. In the latest Recommendations of 2001[1] IUPAC redefined δ and recommends that the chemical shift normally be expressed in ppm. The Author Guidelines have therefore been adjusted accordingly.
[1] NMR Nomenclature, Nuclear Spin Properties and Conventions for Chemical Shifts (IUPAC Recommendations 2001): R. K. Harris, E. D. Becker, S. M. Cabral de Menezes, R. Goodfellow, P. Granger, Pure Appl. Chem. 2001, 73, 1795-1818.

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