Nevertheless, due to its simplicity and lack of ambiguity, the IUPAC recommends use of the expanded octet double-bond structure to depict sulfoxides, rather than the dipolar structure or structures that invoke "no-bond" resonance contributors. The double-bond character of the S−O bond may be accounted for by donation of electron density into C−S antibonding orbitals ("no-bond" resonance forms in valence-bond language). The double-bond resonance form implies 10 electrons around sulfur (10-S-3 in N-X-L notation). The bond between the sulfur and oxygen atoms is intermediate of a dative bond and a polarized double bond. Sulfoxides are generally represented with the structural formula R−S(=O)−R', where R and R' are organic groups. The sulfur center is pyramidal the sum of the angles at sulfur is about 306°. Sulfoxides feature relatively short S–O distances. (1) 3-Dimethylsulphoniopropionate has multiple functions in protecting algae.Structure of DMSO (red = O, yellow = S) as determined by X-ray crystallography of PdBr 2(bipy)♽MSO. But if anyone pins it on you anyhow, just say that you're doing your part in controlling global warming, and all should be good. You now possess the knowledge to deflect blame should you toot one out in the company of others. DMS plays a part in the formation of clouds that block solar radiation from hitting the earth sort of an anti-greenhouse gas. Scientists from the Leibniz Institute for Tropospheric Research have been estimated that marine algae produce 10 to 35 million metric tons of atmospheric sulfur, mostly DMS, which is thought to connect the ecosystems of the sea and air. When it breaks down, dimethyl sulfide is released in huge quantities.ĭMS is the largest source of sulfur in the atmosphere. DMS is a metabolic breakdown product of 3-dimethylsulphoniopropionate, an osmolyte, which algae biosynthesize in order to maintain a constant volume of water in the cell (1). Given that DMS is what gives the ocean its scent, it is not at all surprising that it comes from marine algae. But not twice.)ĭemocrat Point, Fire Island National Seashore, NY Tiny amounts of skatole are used in perfume, but if you open a bottle of the stuff and stick your nose in there (not recommended), it's "Howdy Doody Time." (Some idiot who, by an astounding coincidence, happens to work at ACSH tried this once. One of them is called skatole – the principal odor of feces. There are plenty of chemicals with pleasant scents at low concentrations but jump ugly on you at higher concentrations. "You'll have no problem finding a seat on the bus if you are working with dimethyl sulfide." I was not prepared for this synergistic symphony of scent, and nearly dropped the flask.īut one of his readers chose to accentuate the positive (dimethyl sulfide itself): When these two came together, they produced something that seemed to have come from a robot with gastrointestinal issues. (His " Things I Won't Work With" articles are hilarious and very widely read.) The following quote isn't about DMS itself but something that formed when he mixed it with an organosilane and inadvertently made something even worse) but it's pure gold:
Whenever I write about a nasty chemical, I always look for a quote from Derek Lowe, whose In the Pipeline blog is the place to go for up-to-date information on chemistry, the pharmaceutical universe, health issues, and also humor. The chemical structures of geosmin, butyric acid, and dimethyl sulfide (from left to right). Dimethyl sulfide (DMS) is one of the fart gases, among other things. And the beloved smell of the ocean is due to.dimethyl sulfide, one of the most disgusting odors ever to haunt chemistry labs. The pleasant smell of soil, when it first starts to rain, is due to geosmin, a simple organic molecule that people can detect at extremely low concentrations. The ghastly vomit-like smell of ginkgo berries is caused by butyric acid, giving vomit its lovely bouquet. When chemists hear the word "smell," we also think "chemical" because 1) we're deeply disturbed individuals 2) scents result from a specific chemical or mixture of chemicals, and we wanna know what it is. It doesn't much matter which ocean you're near. Ah! It's summertime, and those of us who happen to be "ocean people" just can't get enough of the wonderful smell of Mother Ocean.
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