Google agreed to its largest acquisition yesterday, reaching a deal to purchase DoubleClick, the online advertising company, from two private equity firms for $3.1 billion in cash, almost double what it paid for YouTube last year. And perhaps just as important, the deal kept DoubleClick from the hands of Microsoft.

For Google, the purchase is another step in its transformation from a search engine into an advertising powerhouse. DoubleClick, which is based in New York City, specializes in software for display advertising and has close relationships with Web publishers, advertisers and advertising agencies.

The sale of DoubleClick involved weeks of negotiation that included at one point Yahoo, AOL and, most prominently, Microsoft, which has been trying to position itself as an advertising rival to Google. Even though Microsoft has more cash on hand than Google,the company was ultimately outbid.

The acquisition will also strengthen Google’s position with respect to Yahoo, its chief rival in Internet search and advertising and a leader in the sale of display ads.

DoubleClick may not be a household name, but it is the most prominent ad serving company on the Web, meaning that it delivers display ads from ad agencies to the sites where they are run.

DoubleClick provides software and services to both Web publishers like MySpace and AOL and to advertisers and agencies, who buy the ads. DoubleClick’s software culls data about Web surfers’ interaction with ads to determine how to place the most effective display ads.

Google, for all its outsize reputation, has made most of its money in the online basics: the text-based search engine and small text ads that are like the Yellow Pages of the online advertising. DoubleClick’s strength, by contrast, lies in flashy banner ads and, more recently, video ads that are more like high-end magazine or television ads. Google has taken steps in the last year to enter display advertising by expanding its AdSense program but has not gained great traction.

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