am taking the liberty in this installment of departing temporarily
from our incompleted subject of Aromatic Compounds in order to
present some other matters that have accumulated that you may find
of interest.
Protein folding in the news
Proteins, when folding as described in Part XVII, sometimes make
mistakes under stressful conditions and form misshapen moieties;
these may possibly lead to brain disorders such as Alzheimer's,
Huntington's, and "mad cow" diseases. As reported in Chemistry 3
(4), Summer 1999, biochemists have discovered "protein police" in
the human organism, called chaperonins, that intercept these
misfolded proteins and set them on the proper course. Without this
policing action we would be subject to more widespread nerve
disorders.
A major digressionTranslating French chemistry to English with
style.
A French chemical paper just translated so abounds with pitfalls for
the unwary translator that it seems worthwhile to explore the proper
nomenclature and terminology to be used, in this translator's
opinion.
Locators in French names of organic chemicals normally follow the
substituent instead of preceding it. Below are some examples of
proper nomenclature (English in italics):
oxazolidinones-2 | 2-oxazolidinones |
oxa-1 oxo-2 diaza-3,8 spiro[4,5] décane |
1-oxa-2-oxo-3,8-diazaspiro[4,5]decane {all one word in English}
|
N-alcoyl pipéridinones | N-alkylpiperidinones
|
p-fluoro phénéthyl-1 pipéridinone-4 | 1-(p-fluorophenylethyl)-4-piperidinone
| bromo-1 (p-fluorophényl)-2 éthane | 1-bromo-2-(p-fluorophenyl)ethane
| chloro-1 (méthylènedioxy-3,4 phényl)-2 éthane | 1-chloro-2-(3,4-methylenedioxyphenyl)ethane
|
Other terminological differences between French and English,
especially in the use of prepositions, also found in this paper
included:
... un cycle oxazolidinique | ... an oxazolidine ring.
|
... transformées par action d'un excès de cyanure de sodium sur la
combinaison bisulfitique de celles-ci, en cyanhydrines
correspondantes ... |
... converted into corresponding cyanohydrins by the action of
excess sodium cyanide on their bisulfite addition products ...
|
... les liqueurs-mères de cristallisation de la base ... |
... the mother liquors from crystallization of the base ...
| ... F(K), Eb/0.6 |
... m.p. (Koefler), b.p. (0.6 mm) ...
| ... halogénures d'alcoyles ...
| ... alkyl halides ...
| ... préparée à partir de A avec un rendement de x% ...
| ... prepared from A in a yield of x% ...
| ... Ni Raney ...
| ... Raney nickel ... |
... brut(e) ... | ... crude ...
| ... Ensuite on refroidit et extrait l'huile surnageante au
chloroforme, lave à l'eau, puis avec une solution de NaHCO3 à 10%, sèche sur Na2SO4, et chasse le chloroforme sous pression réduite ...
| ... It is then cooled, and the supernatant oil is extracted with
chloroform, washed with water and then with a 10% NaHCO3 solution, dried over Na2SO4, and the chloroform is evaporated under reduced
pressure ...
| ... recristallisé dans ... or
... recristallisé de ...
| ... recrystallized from ...
| ... repris avec éther ...
| ... taken up in ether ...
| ... purifiée par transformation en chlorhydrate au sein de methanol
à 95% ...
| ... purified by conversion into the hydrochloride in 95% methanol
...
| ... On fait barbotter un courant de HCl sec jusqu'à reaction acide
des jus ...
| ... A stream of dry HCl is bubbled through until the liquid is
acidic ...
|
Another digressionempirical formulas and Calc./Found calculations
How often have you received a fax with teeny-weeny empirical
formulas (e.g. C14H19N3O2) but you cannot read the numbers? There is
help. Normally these appear in the Experimental Part of a paper
along with the calculated percentages of each element (except
oxygen).
Compuserve's Science/Math forum contains two QBasic (or QuickBasic)
programs I originally wrote for the Commodore 64, named formula.bas
and analysis.bas. They are self-explanatory when run.
With formula.bas, you enter the published calculated percentages of
all of the elements in the compound (except oxygen), which almost
always are in a larger font and are legible, for example C 64.34, H
7.33, N 16.08 for the compound given above, and the program
instantly returns the empirical formula, including oxygen. If the
result looks strange, there is an option to keep searching for the
proper formula.
Conversely with analysis.bas, you enter the faxed empirical formula
(which you may have to guess), and the program returns the
percentages of each element. This is useful if the calculated
percentages of only some of the elements are given, and you have to
guess at the faxed formula. The program will confirm or exclude your
guess by comparison with the calculated percentages in the document.
By trial and error, the correct formula can be found.
If you have difficulty running these Basic programs (or have
forgotten how in the Windows Revolution), contact the author at
cclaff@cs.com for help.
Abbreviations for substituents
Chemists like to abbreviate almost everything to save pencils and
energy. Below is a short list of some of the most common
abbreviations for substituents with their spelled-out meanings:
Me | methyl | | CH3-
|
Et | ethyl | | C2H5-
|
Pr | n-propyl | | n-C3H7-
|
Bu | n-butyl | | n-C4H9-
|
Ph | phenyl | | C6H5-
|
Bzl | benzyl | | C6H5CH2-
|
Bz | benzoyl | | C6H5C(=O)-
|
Boc | t-butoxycarbonyl | | t-C4H9OC(=O)-
|
Cbz | benzyloxycarbonyl | | C6H5CH2OC(=O)-
|
Tos (or Ts) | p-toluenesulfonyl | | p-H3CC6H4SO2-
| Ac | acetyl | | CH3C(=O)-
| Trt | triphenylmethyl (or trityl) | | (C6H5)3C-
|
Chirality in 3D
A free program that can be downloaded from the Internet, called
RasMol, allows chemical formulas to be shown as stick models, ball-and-stick models, space-filling models, or even in stereoscopic 3-D
form, in brilliant colors. The 3-D option in particular provides
images that are spectacular for those able to view them. Alas, I
have e-mailed samples to several renowned colleagues, none of whom
are able to cross their eyes voluntarily to see these images in all
their splendor. As a broader test, I am attaching images below of
(R)-2-butanol and (S)-2-butanol. Each of these consists of two
images with slightly different perspectives. When the two images are
fused by crossing your eyes, a third image in the center floats in
air between the viewer and the screen, and the difference between
the two enantiomers can be seen clearly. I would appreciate any
positive or negative feedback on your success, via e-mail
cclaff@cs.com.
If your eyes will not voluntarily cross, try placing your index
finger between the two images of either isomer, focus on the
fingernail, and slowly draw your finger toward you while keeping the
images in view. A third image should form, and with patience, should
come into focus.
I expect to resume discussion of aromatic hydrocarbons in Part XIX.
|