Electronic Lab Notebooks- More organised, streamlined, secure and easier to search and share..??

For the past 6 years I worked as a research scientist in pharma industry working on synthesis of various molecules.  All these years I documented the procedures in paper based notebooks and ended up having several sets of notebooks.  Now today all of a sudden I started thinking why don’t we start using electronic lab notebooks.  I feel they can be organised much more easily and stored much more securely than the physical books which we generally use.

Also it makes searching of procedures easier for us.  Say you want search for a particular conversion lets say you want synthesise 2-formyl indole and someone from your company might have already worked on it which you don’t know.  Instead of searching on Scifinder (for which u have to pay) or internet, you can start the initial search with your in-house procedures first i.e. with the help of electronic lab note book.  This makes your search a lot easier.

I haven’t personally used any electronic lab notebook till now and also feel they are more expensive for any small pharma company to afford and maintain them, but thanks to the software companies who create these.  We have basic versions of e-LNB available on internet for free.  We can always upgrade to more advanced version with enhanced features but for a price.

If anyone of you reading this has the experience of using a e-LNB please put in your experiences working with them. 

I also feel paper based lab notebooks are the best sometimes as it presents our work in real synonymous with our mind while working…J

Some of the freely available ELNB on internet have been listed below for your convenience.

http://www.labtrack.com/
http://www.aejournal.net/content/1/1/4
http://www.contur.com/home/
http://www.sparklix.com/
http://accelrys.com/products/eln/

For a detailed review of various e-LNB available in market you can visit the following publication from Journal of Laboratory Automation.  Click here..>

Acyloin Condensation

Acyloin Condensation is a coupling reaction in which two carboxylic acid esters couple in the presence of metallic sodium under inert atmosphere to yield an α-hydroxyketone (also known as acyloin).

This reaction is favoured when R is an long chain alkyl group and also when high boiling solvents are used. Intramolecular condensation also takes place leading to closed rings of different sizes (like paracyclophanes or catenanes). But again this all depends on ring size and steric properties, but independent from high dilution. Intramolecular cyclisation over intermolecular polymerisation in diesters.

If the condensation is carried out in the presence of proton donor like alcohol then reduction of ester to alcohol takes place. This reaction is also called as Bouveault-Blanc Reduction.

Mechanism of Acyloin Condensation

Above mechanism involves

(1) Oxidative ionization of two sodium atoms on the double bond of two ester molecules.

(2) Free radical coupling between two molecules of the homolytic ester derivative (A Würtz type coupling). Alkoxy-eliminations in both sides occur, producing a 1,2-diketone.

(3) Oxidative ionization of two sodium atoms on both diketone double bonds. The sodium enodiolate is formed.

(4) Neutralization with water to form the enodiol, which tautomerizes to acyloin.

The enediolate intermediate is trapped as the bis-silyl derivative by the use of trapping agent chlorotrimethylsilane. This intermediate can be isolated and subsequently hydrolysed under acidic condition to the acyloin, which gives a better overall yield. Toluene, dioxane, THF or dialkylethers may be used and in some cases NMP (I am not sure of this) may also be used.

Literature references:

(1) Acyloin condensation in which chlorotrimethylsilane is used as a trapping agent
     Organic Syntheses, Coll. Vol. 6, p.167 (1988); Vol. 57, p.1 (1977).

(2) The Acyloin Condensation of Aralkyl Esters
      J. Am. Chem. Soc., 1952, 74 (19), pp 4861–4864

(3) The Formation of Five- and Six-membered Rings by the Acyloin Condensation.
      J. Am. Chem. Soc., 1957, 79 (22), pp 6050–6055

(4) Mechanism of the acyloin condensation
     J. Org. Chem., 1975, 40 (4), pp 393–402